唾液酸N-苯基三氟乙酰亚胺酯和苯基炔酸酯为给体的糖苷化研究
|
摘要
N-乙酰神经氨酸(Neu5Ac)是一类自然界中分布最广的唾液酸类化合物,它位于哺乳动物细胞表面糖蛋白和糖脂的末端。在人体内,N-乙酰神经氨酸往往以α(2→3)或者α(2→6)唾液酸苷键与半乳糖和N-乙酰半乳糖连接。细胞表面的Neu5Ac在细胞间的相互作用中起到了重要的作用,例如病原体-宿主的识别、肿瘤的转移、毒素-受体的相互作用、细胞的分化和增殖。为了进一步研究它们的生物功能,发展有效和区域选择性的合成α(2→3)和α(2→6)-Neu5Ac-Gal单元的路线是非常必要的。
一以唾液酸三氟乙酰亚胺酯为给体高效合成 Neu5Acα(2→3)-Gal模块,并将其应用于神经节苷脂GM3的合成
本文对以唾液酸三氟乙酰亚胺酯为给体,设计合成了不同的半乳糖受体,进行糖苷化反应研究。获得了一条有效合成Neu5Acα(2→3)-Gal单元的路线,用2,3,4-羟基裸露的半乳糖为受体,TBSOTf作为催化剂进行糖苷化反应,并找到了最佳的一个半乳糖受体2-(trimethylsilyl)ethyl 6-O-tert-butyldiphenylsilyl-β-D- galactopyranoside(75g),以73%的收率和89%的立体选择性合成了Neu5Acα(2→3)-Gal糖苷键,并将得到的二糖模块成功的应用于GM3的合成。
二唾液酸苯基炔酸酯为给体的糖苷化研究
一种新的以唾液酸炔基苯甲酸酯为给体,以Au(I)为催化剂,四氢呋喃为溶剂的唾液酸苷化方法被发现,并将其应用于唾液酸糖苷的合成中得到了比较理想的效果。合成的炔酯给体可以直接使用,而且稳定性好;糖苷化的产率较高;促进剂是催化量的,催化体系是中性的,可以有效抑制消除产物的生成。
N-Acetylneuraminic acid (Neu5Ac), the most abundant sialic acid congener in nature, is found at the termini of glycoproteins and glycolipids on mammalian cell surfaces. In humans, Neu5Ac occurs frequently via aα(2→3) glycosidic linkage to galactose orα(2→6) linkages to galactose and N-acetylgalactosamine. Since Neu5Ac on the cell surfaces plays diverse and important roles in cell-cell interaction processes, such as pathogen-host recognition, tumor metastasis, toxin-receptor interaction, malignant alteration, cell differentiation and proliferation, much effort has been devoted to the efficient and stereoselective synthesis ofα(2→3) andα(2→6)-Neu5Ac-Gal units in order to further investigate their biological functions.
1. Efficient Synthesis of a Sialic Acidα(2→3) Galactose Building Block using N-phenyltrifluoroacetimidate as leaving group and Its Application to the Synthesis of Ganglioside GM3.
Glycosylation of various galactose derivatives with O-acetylated sialic acid N-phenyltrifluoroacetimidate as the donor was investigated. Efficientα(2→3) sialylation of galactose, with up to 73% yield and 8.4:1 stereoselectivity, was realized when 2,3,4-unprotected galactose derivatives and TBSOTf were used as acceptors and promoter, respectively. Sialylation of 2-(trimethylsilyl)ethyl 6-O-tert -butyldiphenylsilyl-β-D-galactopyranoside gave the best result, and the resultant Neu5Acα(2→3) Gal disaccharide was successfully used to synthesize ganglioside GM3.
2. Study on sialylation using ortho-alkynylbenzoate as donors
A novel sialylation method was investigated, which using ortho-alkynylbenzoates as the donor, Au(I) as promoter and THF as the solvent, showed favorability compared with previous protocols for direct sialylation. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.
一以唾液酸三氟乙酰亚胺酯为给体高效合成 Neu5Acα(2→3)-Gal模块,并将其应用于神经节苷脂GM3的合成
本文对以唾液酸三氟乙酰亚胺酯为给体,设计合成了不同的半乳糖受体,进行糖苷化反应研究。获得了一条有效合成Neu5Acα(2→3)-Gal单元的路线,用2,3,4-羟基裸露的半乳糖为受体,TBSOTf作为催化剂进行糖苷化反应,并找到了最佳的一个半乳糖受体2-(trimethylsilyl)ethyl 6-O-tert-butyldiphenylsilyl-β-D- galactopyranoside(75g),以73%的收率和89%的立体选择性合成了Neu5Acα(2→3)-Gal糖苷键,并将得到的二糖模块成功的应用于GM3的合成。
二唾液酸苯基炔酸酯为给体的糖苷化研究
一种新的以唾液酸炔基苯甲酸酯为给体,以Au(I)为催化剂,四氢呋喃为溶剂的唾液酸苷化方法被发现,并将其应用于唾液酸糖苷的合成中得到了比较理想的效果。合成的炔酯给体可以直接使用,而且稳定性好;糖苷化的产率较高;促进剂是催化量的,催化体系是中性的,可以有效抑制消除产物的生成。
N-Acetylneuraminic acid (Neu5Ac), the most abundant sialic acid congener in nature, is found at the termini of glycoproteins and glycolipids on mammalian cell surfaces. In humans, Neu5Ac occurs frequently via aα(2→3) glycosidic linkage to galactose orα(2→6) linkages to galactose and N-acetylgalactosamine. Since Neu5Ac on the cell surfaces plays diverse and important roles in cell-cell interaction processes, such as pathogen-host recognition, tumor metastasis, toxin-receptor interaction, malignant alteration, cell differentiation and proliferation, much effort has been devoted to the efficient and stereoselective synthesis ofα(2→3) andα(2→6)-Neu5Ac-Gal units in order to further investigate their biological functions.
1. Efficient Synthesis of a Sialic Acidα(2→3) Galactose Building Block using N-phenyltrifluoroacetimidate as leaving group and Its Application to the Synthesis of Ganglioside GM3.
Glycosylation of various galactose derivatives with O-acetylated sialic acid N-phenyltrifluoroacetimidate as the donor was investigated. Efficientα(2→3) sialylation of galactose, with up to 73% yield and 8.4:1 stereoselectivity, was realized when 2,3,4-unprotected galactose derivatives and TBSOTf were used as acceptors and promoter, respectively. Sialylation of 2-(trimethylsilyl)ethyl 6-O-tert -butyldiphenylsilyl-β-D-galactopyranoside gave the best result, and the resultant Neu5Acα(2→3) Gal disaccharide was successfully used to synthesize ganglioside GM3.
2. Study on sialylation using ortho-alkynylbenzoate as donors
A novel sialylation method was investigated, which using ortho-alkynylbenzoates as the donor, Au(I) as promoter and THF as the solvent, showed favorability compared with previous protocols for direct sialylation. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.
引文
1.叶新山.化学糖生物学―新兴的前沿研究领域,21世纪有机化学发展战略,杜灿屏,刘鲁生,张恒主编,第一版,北京,化学工业出版社,2002,307.
2. www.google.com/multivalency in carbohydrate chemistry.
3.俞飚,金城.糖的化学和生物科学,21世纪有机化学发展战略,杜灿屏,刘鲁生,张恒主编,第一版,北京,化学工业出版社,2002,298.
4. Schnaar, R.L. Adv.Pharmacol.(San Diego) 1992, 23, 35-84
5. a) Springer, T. A.; Lasky, L. A. Nature, 1991, 349, 196. B) Lasky, L. A. Science, 1992, 258, 964. C) Rice, G. E.; Bevilacqua, M. P.; Science 1989, 246-1303. D) Bevilacqua, M. P.; Stengeling, S.; Gimbrone, M. A.; Seed, J. B. Science 1989, 243, 1160.
6. a) Phillips, M. L.; E. Nudelman, F. C.; Gaeta, A.; Perez, M.; Singhal, A. K.; Hakomori, S. I. Science 1990, 250, 1130; b) G. Waltz, A.; Arufto, W.; Kolanis, M.; Bevilacqua; B. Seed, Science 1990, 250, 1132. C) Lewe, J. B.; Stoolman, L. M. Cell.1990, 63, 475.
7. a) Ichikawa, Y.; Shen, G. J.; Wong, C. H. J. Am. Chem. Soc. 1991, 113, 4698-4700. B) Ichikawa, Y.; C. Liu, J. L.; Shen, G. J.; Wong, C. H. J. Am. Chem. Soc. 1991, 113,6300-6302. C) Ichikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G. J.; Junceda, E. G.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C. H. J. Am.Chem. Soc. 1992, 114, 9283-9298.
8. Molean, J. Am. J. Physiol. 1916, 41, 250-257.
9. Capila, I.; Lindhardt, R. J. Angew. Chem. Int. Ed. 2002, 1, 390-412.
10. a) Bockel, C. A. A. van; Petitou, M. Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1690; b) Petitou, M.; Bockel, C. A. A. van Angew. Chem. Int. Ed. 2004, 43, 3118-3133.
11. Drak, J; Iwasawa, N; Danishefsky, S.J; Crothers, D.M. Proc.Natl.Acad.Sci.USA 1991, 88, 7464.
12. Ge, M; Chen, Z; Kahne, D. Science 1999, 284, 507.
13. Nicolaou, K. C.; Mitchell, H. J.; Suzuki, H.; Rodrìguez, R. M.; Baudoin, O.; Fylaktakidou, K.C. Angew. Chem. Int. Ed. 1999, 38, 3334.
14.金城.糖生物学:基因组学和蛋白质组学的延伸,世界科技研究与发展, 2000, 23(2), 31。
15. Zhang Z.; Ollmann I. R.; Ye X. S.; Wischnat R.; Baasov T.; Wong C. H. J. Am. Chem. Soc.1999, 121, 734.
16. Plante O. J.; Palmacci E. R.; Seeberger P. H. Science. 2001, 291, 1523.
17. Bronislaw L. Slomiany, Varahabhotla L. N. Murty, Yun H. Liau et al, Animal Glycoglycerolipids, Prog. Lipid Res., 1987, 26 , 29-51.
18. Sweeley, CC.; Siddiqui, B. Chemistry of mammalian glycolipids. In: Horowitz MI, Pigman W, eds. The Glycoconjugates. New York: Academic Press, 1977, Vol I. 459-540.
19.陈惠黎,王克夷,糖复合物的结构和功能,第一版,上海:上海医科大学出版社, 1997, 164-209.
20. William Curatolo, The physical properties of glycolipids, Biochibica et Biophysica Acta, 1987, 906, 111-136.
21. William Curatolo, Glycolipid function, Biochibica et Biophysica Acta, 1987, 906, 136-160.
22. Teruyuki Sakai, Yasuhiko Koezuka, Glycolipid derivatives as therapeutic agents, Exp. Opin. Ther. Patents, 1999, 9(7), 917-930.
23. Zeller CB and Marchase RB.Am J Physiol, 1992; 262; C1341.
24.吴谷盛.神经节苷脂在神经组织中的功能与作用机理.细胞生物化学杂志,1986,823.
25.唐向东,佟振清,杨文俊,生命的化学,1994; 14(3); 25-27.
26. Geisler Fh, Dorsey FC and Coleman WP.N Engl Med, 1991; 324; 1829.
27.小仓治夫,古火田公夫.シアル酸诱导体の合成.有机合成化学会志1984;42:536
28. M. J. Horowitz, W. Pigman, the Glycoconjugates Academic Press, New York, 1978, vol I and II.
29. Schauer, R.; Kamerling, J. P. In Glycoproteins II; Montreuil, J.,Vliegenthart, J. F. G., Schachter, H., Eds.; Elsevier: Amsterdam, 1997; pp 243-402.
30. Biology of the Sialic Acids; Rosenberg, A., Ed.; Plenum Press: New York, 1995.
31. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131-234.
32. Varki, A. Glycobiology 1993, 3, 97-130.
33. Sialic Acids: Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer-Verlag: Wein, 1982; Vol. 10.
34. A. Varki, Glycobiology 1993, 3, 97.
35. M. Von Itzstein; W. Y. Wu; G. B. Kok; etal. Nature, 1993, 363, 418-423.
36. C. U. Kim; W. Lew; M. A. Willians; etal. J. Am. Chem. Soc. 1997, 119, 681-690.
37. Taki, T.; Hirabayashi, Y.; Ishikawa, H.; Ando, S.; Kon, K.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075-3078.
38. Hirabayashi, Y.; Hamaoka, A.; Matsumoto, M.; Matsubara, T.; Tagawa, M.; Wakabayashi, S.; Taniguchi, M. J. Biol. Chem. 1985, 260, 13328-13333.
39. Bremer, E. G.; Hakomori, S.; Bowen-Pope, D. F.; Ralnes, E.; Ross, R. J. Biol. Chem. 1984, 259, 6818-6825.
40. For a review see: Gangliosides and Cancer; Oettgen, H. F., ed.; VCH, N.Y., 1989.
41. Portoukalian, J.; Zwinglstein, G.; Dore, J.-F.; Borgion, J. J. Biochem. 1976, 56, 1285.
42. Yamakawa, T.; Suzuki, S. J. Biochem. (Tokyo), 1952, 39, 383.
43. a) Hanai, N.; Nores, G. A.; MacLeod, C.; Torres-Mendez, C. R.; Hakomori, S. J. Biol. Chem.` 1988, 263, 10915-10921. b) Bremer, E.; Schlessinger, J.; Hakomori, S. J. Bio. Chem. 1986, 261, 2434.
44. Roy, R. Design and Syntheses of Glycoconjugates. In Modem Methods in Carbohydrate Synthesis; Khan, S. H., O'Neil, R., Eds.; Harwood Academic, Amsterdam, 1996, pp. 378-402.
45. a) Gamian, A.; Chomik, M.; Laferri~re, C. A.; Roy, R. Can. J. Microbiol. 1991, 37, 233-237; b) Roy, R.; Andersson, F.O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem` Int. Ed. EngL 1992, 31, 1478-1481; c) Spaltenstein, A.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 686-687.
46. a) Sugimoto, M.; Ogawa, T. Glycoconjugate J. 1985, 2, 5-9; b) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1989, 188, 71-80; c) Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25; d) LOnn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116; e) Ray, A. K.; Nilsson, U.; Magnusson, G. J. Am. Chem. Soc. 1992, 114, 2256-2257; f) Ercegovic, T.; Magnusson, G. J. Chem` Soc. Chelr. Commun. 1994, 831-832; g) Lui, K. K.-C.; Danishefsky, F. J. Am. Chem. Soc. 1993, 115, 4933-4934; h) Ito, Y.; Paulson, J. C. J. Am. Chem. Soc. 1993, 115, 1603-1605; i) Ercegovic, T.; Magnusson, G. J. Org. Chem. 1995, 60, 3378-3384.
47. a) A. Gottschalk, Nature 1951, 167, 845; b) A. Gottschalk, Nature 1955, 176, 881.
48. M. J. Horowitz, W. Pigman, the Glycoconjugates Academic Press, New York, 1978, vol I and II.
49. Schauer, R. Sialic Acids; Chemistry, Metabolism and Function Vol. 10, Springer-Verlag, NewYork City, 1982.
50. a) Okamoto, K.; Goto, T. Tetrahedron 1990, 46, 5835-5857; b) M. P. Deninno, Synthesis. 1991, 583; c) G.-J. Boons, A. V. Demchenko, Chem. Rev. 2000, 100, 4539.
51. Sina?, P. Pure Appl. Chem. 1991, 63, 519-528.
52. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
53. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173-200.
54. Boons, G. J. Tetrahedron 1996, 52, 1095-1121.
55. Whitfield, D. M.; Douglas, S. P. Glycoconjugate J. 1996, 13, 5-17.
56. Veeneman, G. H. In Carbohydrate Chemistry; Boons, G., Ed.; Blackie Academic & Professional: London, 1998; pp 98-174.
57. Schmidt, R. R.; Castro-Palomino, J. C.; Retz, O. Pure Appl. Chem. 1999, 71, 729-744.
58. DeNinno, M. P. Synthesis 1991, 583-593.
59. a) W. Koenigs, E. Knorr, Chem. Ber. 1901, 34, 957; b) K. Igarashi, Adv. Carbohydr. Chem. Biochem. 1977, 34, 243; c) B. Helferich, Zirner, J. Chem. Ber. 1962, 95, 2604.
60. H. Paulsen, Angew. Chem. Int. Ed. Eng. 1982, 21, 155.
61. a) R. R. Schmidt, M. Reichrath, Angew. Chem. Int. Engl. 1979, 18, 466; b) F. Paquet, P. Sin?y, J. Am. Chem .Soc. 1984, 106, 8313; c) D. Crich, T. Ritchie, J. Chem. Soc., Chem. Commun. 1988, 1461.
62. Ito, Y.; Gaudino, J. J.; Paulson, J. C. Pure Appl. Chem. 1993, 65, 753-762.
63. von Itzstein, M.; Thomson, R. J. Topics Curr. Chem. 1997, 186, 119-170.
64. Hasegawa, A.; Okhi, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res., 1991, 212, 277.
65. Hasegawa, A.; Nagahama, T.; Okhi, H.; Hotta, K.; Ishida, H.; Kiso, M. J. Carbohydr. Chem., 1991, 10, 493-498.
66. Cao, S.; Meunier, S.; Andersson, F.; Letellier, M.; Roy, R. Tetrahedron Asymmertry, 1994, 5, 2303.
67. Roy, R. Topics Curr. Chem. 1997, 187, 241-274.
68. Nicolaou, K. C.; Bockovich, N. J. In Bioorganic Chemistry: Carbohydrates; Hecht, S., Ed.; Oxford University Press: New York, Oxford, 1999; pp 134-173.
69. Hasegawa, A. In Synthetic Oligosaccharides; Kovac, P, Ed.; 1994; Vol. 560, pp 184-197.
70. Schmidt, R. R. In Synthetic Oligosaccharides; Kovac, P., Ed.; 1994; Vol. 560, pp 276-296.
71. Fraser-Reid, B.; Madsen, R.; Campbell, A. S.; Roberts, C. S.; Merritt, R. J. In Bioorganic Chemistry: Carbohydrates; Hecht, S., Ed.; Oxford University Press: New York, Oxford, 1999; pp 89-133.
72. Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
73. Kanie, O.; Ogawa, T.; Ito, Y. J. Synth. Org. Chem., Jpn. 1998, 56, 952-962.
74. a) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1988, 184, C1-C4; b) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1989, 188, 71-80; c) Murase, T.; Kameyama, A.; Kartha, K. P. R.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1989, 8, 265-283; d) Kanie, O.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1988, 7, 501-506.
75. a) Ito, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1998, 306, 581-585; b) Ehara, T.; Kameyama, A.; Yamada, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1996, 281, 237-252. c) Roy, R.; Andersson, F. O.; Letellier, M. Tetrahedron Lett. 1992, 33, 6053-6056. d) Kiso, M.; Ando, K.; Inagaki, H.; Ishida, H.; Hasegawa, A. Carbohydr. Res. 1995, 272, 159-178.
76. a) Ding, Y.; Fukuda, M.; Hindsgaul, O. Bioorg. Med. Chem. Lett. 1998, 8, 1903-1908; b) Ando, H.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1999, 18, 603-607; c) Ando, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1997, 300, 207-217.
77. a)Liebe, B.; Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778; b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. O.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616-1634; c) Cao, S.; Meunier, S. J.; Andersson, F. O.; Letellier, M.; Roy, R. Tetrahedron: Asymmetry 1994, 5, 2303-2312; d) Ellervick, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314-9322; e) Ellervick, U.; Grundberg, H.; Magnusson, G. J. Org. Chem. 1998, 63, 9323-9338; f) Salvatore, B. A.; Prestegard, J. H. Tetrahedron Lett. 1998, 39, 9319-9322; g) Tietze, L. F.; Janssen, C. O.; Gewert, J. A. Eur. J. Org. Chem. 1998, 1887-1894.
78. a) A. Marra, P. Sina?, Carbohydr. Res. 1990, 195, 303; b) W. Birberg, H, L?nn, Tetrahedron Lett. 1991, 32, 7453; c) V. Martichonok, G. Whitesides, J. Org. Chem. 1996, 61, 1702; d) J.-R. Pougny, P. Sina?, Tetrahedron Lett. 1976, 45, 4073; e) A. J. Raccliffe, B. Fraser-Reid, J. Chem. Soc., Perkin Trans I 1990, 747; f) I. Braccini, C. Derouet, J. Esnault, C. Herre du Penhoat, J.-M. Mallet, V. Michon, P. Sina?, Carbohydr. Res. 1993, 246, 23.
79. H. Kondo, Y. Ichikawa, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 8748-8750.
80. T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123-6126.
81. Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25.
82. a) Singh, K.; Fernandez-Mayoralas, A.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775-776; b) Coteron, J. M.; Singh, K.; Asensio, J. L.; Domingues-Dalda, M.; Fernandez-Mayoralis, A.; Jimenez-Barbero, J.; Martin-Lomas, M. J. Org. Chem. 1995, 60, 1502-1519.
83. a) Schmidt, R. R. In Synthetic Oligosaccharides; Kovac, P., Ed.; 1994; Vol. 560, pp 276-296; b) Greilich, U.; Brescello, R.; Jung, K. H.; Schmidt, R. R. Liebigs. Ann. 1996, 663-672.
84. M. Adinolfi, G. Barone, A. Iadonisi, M. Schiattarella, Synlett 2002, 269-270.
85. a) B. Yu, H. Tao, Tetrahedron lett. 2001, 42, 2405-2407; b) B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099-9102; c) S. Cai, B. Yu, Org. Lett. 2003, 21, 3827-3830.
86. a) K. Uneyama, J. Fluo. Chem. 1999, 97, 11; b) K. Tamura, H. Mizukami, K. Maeda, H. Watananbe, K. Uneyama, J. Org. Chem. 1993, 58, 32-35.
87. R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.
88. R. R. Schmidt, Pure & Appl. Chem. 1989, 61, 1257-1270.
89. a) R. R. Schmidt, H. Gaden, H. Jatzke, Tetrahedron Lett. 1990, 31, 327-330; b) R. R. Schmidt, J. Michel, M. Roos, Lieb. Ann. Chem. 1984, 1343-1357.
90.陶厚朝硕士论文,中国科学院上海有机所,2002.
91. L. A. Mulard, C. Costachel, P. J. Sansonetti, J. Carbohydr. Chem. 2000, 19, 849-877.
92. a) R. R. Schmidt, W. Kinay, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21; b) R. R. Schmidt, K.-J. Jung, In Preparative Carbohydrate Chemistry, S. Hanessian Ed., Marcel Dekker: New York, 1997, p 283.
93. a) Takahashi, T.; Tsukamoto, H.; Yamada, H.; Tetrahedron Lett. 1997, 38, 8223; b) Ye, X.; Huang, X.; Wong, C.H. Chem. Comm., 2001, 974-975; c) Haberman, J.M,; Gin, D.Y. Org. Let. 2001, 3(11), 1665-1668; d) Haberman, J.M,; Gin, D.Y. Org. Let. 2003, 5(14), 2539-2541; e) Koketsu, M.; Balagurunathan, K.; Linhard, R.J. Org. Let., 2000, 2, 3361.
94. a) Okamoto, k.; Knodo, T.; Goto, T. Tetrahadron Lett., 1986, 27, 5233; b) Okamoto, k.; Knodo, T.; Goto, T.` Tetrahadron Lett., 1987, 28, 5919; c) Okamoto, k.; Knodo, T.; Goto, T. Bull. Chem. Soc. Jpn., 1987, 60, 637.
95. a) Castro-Palomino, J. C.; Tsvetkov, Y. E.; Schmidt, R. R. J. Am. Chem. Soc. 1998, 120, 5434-5440; b) Castro-Palomino, J. C.; Tsvetkov, Y. E.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 6837-6840.
96. a) Ito, Y.; Ogawa, T. Tetrahadron Lett., 1988, 29, 3987; b) Kononov, L. O.; Ito, Y.; Ogawa, T. Tetrahadron Lett., 1997, 38, 1599.
97. a) Ercegovic, T.; Magnusson, G. J. J. Org. Chem., 1995, 60, 3378; b) Hossain, N.; Magnusson, G. J. Tetrahadron Lett., 1999, 40, 2217; c) Martinchonok, V.; Whitesidex, G. M. J. Am. Chem. Soc., 1996, 118, 8187;
98. Ye, D.; Liu, W.; Zhang, D.; Feng, E.; Jiang, H.; Liu, H. J. Org. Chem. 2009, 74, 1733-1735;
99. a) Demchenko, A. V.; Boons, G.-J. Tetrahadron Lett., 1998, 39, 3065; b) Demchenko, A. V.; Boons, G.-J. Chem. Eur. J., 1999, 5, 1278; c) De Meo, C.; Demchenko, A. V.; Boons, G.-J. J. Org. Chem., 2001, 66, 5490;
100. Meo, C. D.; Priyadarshani, U. Carbohydr. Res. 2008, 343, 1540-1552;
101. Crich, D.; Li, W.; J. Org. Chem. 2007, 72, 2387-2391;
102. M. Sugimoto and T. Ogawa, Glycoconjugate J., 2 (1985) 5-9.
103. J.F.G. Vliegenthart and J.P. Karnerling, in R. Schauer, (Ed.), Sialic Acids-Chemistry, Metabolism and Function, Cell Biology Monographs, Vol. 10, Springer, New York, 1982, pp 59-76.
104. (a) R.R. Schmidt and E. Riicker, Tetrahedron Lett., 1980, 211, 421-1424; (b) R.R. Schmidt and J. Michel, J. Carbohydr. Chem., 1985, 4, 141-169; (c) R.R. Schmidt, M. Behrendt, and A. Toepfer, Synlett, 1990, 694-696; (d) R.R. Schmidt, in H. Ogura, A. Hasegawa, and T. Suami (Eds.), Carbohydrates- Synthetic Methods and Applications in Medicinal Chemistry., Kodansha, Tokyo, 1992, 66-88.
105. A. Hasegawa, K. Adachi, M. Yoshida, and M. Kiso, Carbohydr. Res., 1992, 230, 273-288.
106. H. Prabhanjan, K. Aoyama, M. Kiso, and A. Hasegawa, Carbohydr. Res., 1992, 233, 87-99.
107. a) A. Marra and P. Sinai, Carbohydr. Res., 1989, 187, 35-42; b) A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, and M. Kiso, Carbohydr. Res., 1991, 212, 277-281; c) A. Hasegawa, K. Adachi, M. Yoshida, and M. Kiso, Carbohydr. Res., 1992, 230, 257-272.
108. T. Kondo, H. Abe, and T. Goto, Chem. Lett., (1988) 1657-1660.
109. a) Y. Ito and T. Ogawa, Tetrahedron Lett., 28 (1987) 6221-6224; b) Y. Ito and T. Ogawa,Tetrahedron, 46 (1990) 89-102.
110. K. Okamoto, T. Kondo, and T. Goto, Bull. Chem. Soc. Jpn., 60 (1987) 631-636.
111. a) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron Lett., 27 (1986) 5229-5232; b) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron Lett., 27 (1986) 5233-5236; c) K. Okamoto, T. Kondo, and T. Goto, Chem. Lett., (1986) 1449-1452; d) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 43 (1987) 5909-5918; e) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 43 (1987) 5919-5928; f) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 44 (1988) 1291-1298; g) K. Okamoto and T. Goto, Tetrahedron, 46 (1990) 5835-5857.
112. a) Uneyama, K. J. Fluo. Chem. 1999, 97, 11; b) Tamura, K.; Mizukami, H.; Maeda, K.; Watananbe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32-35.
113.阮晓红论文,中国海洋大学
114. Adinolfi, M.; Iadonisi, A.; Ravida, A.; Schiattarella, M. J. Org. Chem. 2005, 70, 5316-5319.
115.蔡苏棠论文,中国科学院上海有机所
116. Boons, G. J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539-4565;
117. Shull, B. K.; Wu, Z.; Koreeda, M. J. Carbohydr. Chem. 1996, 15, 955;
118. Li, Y.; Wu, Y. Liebigs Ann. Chem. 1996, 2079;
119. Du, W.; Gervay-Hague, J. Organic Lett. 2005, 7, 2063-2065;
120. Koerner Jr. T. A. W.; Prestegard, J. H.; Demou, P. C.; Yu, R. K. Biochemistry 1983, 22, 2676-2687;
121. Hotha, S.; Kashyap, S. J.Am. Chem. Soc. 2006, 128, 9620-9621;
122. Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604-3608;
123. (a): Sashida, H.; Kawamukai, A. J. Heterocycl. Chem. 1998, 35, 165-167; (b): Bytschkov, I.; Siebeneicher, H.l Doye, S. Eur. J. Org. Chem. 2003, 68, 2888-2902.
124. Wang, P.; Kim, Y.; Navarro-Villalobos, M.; Rohde, R. D.; Gin, D. Y. J. Am. Chem. Soc. 2005, 127, 3256-3257.
125. Al-Sa’Ady, A. K.; McAuliffe, C. A.; Parish, R. V.; Sandeank, J. A. Inorg. Synth. 1985, 191-194;
126. Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem. 1988, 7, 453.
127. Nieto-Oberhuber, C.; Perez-Galan, P.; Herrero-Gomez, E.; Lauterbach, T.; Rodriguez, C.;Lopez, S.; Bour, C.; Rosellon, A.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269-279.
128. Meo, C. D.; Farris, M.; Ginder, N.; Gulley, B.; Priyadarshani, U.; Woods, M. Eur. J. Org. Chem. 2008, 3673-3677.
129. Beaulieu, F.; Ouellet, C.; R.uediger, E. H.; Belema, M. etal. Biooraganic Med. Chem. Lett. 2007, 17, 1233-1237;
130. Okamoto R.; Souma, S.; Kajihara, Y. J. Org. Chem. 2008, 73, 3460-3466;
131. Meo. C. D.; Priyadarshani, U. Carbohydr. Res. 2008, 343, 1540-1552.
2. www.google.com/multivalency in carbohydrate chemistry.
3.俞飚,金城.糖的化学和生物科学,21世纪有机化学发展战略,杜灿屏,刘鲁生,张恒主编,第一版,北京,化学工业出版社,2002,298.
4. Schnaar, R.L. Adv.Pharmacol.(San Diego) 1992, 23, 35-84
5. a) Springer, T. A.; Lasky, L. A. Nature, 1991, 349, 196. B) Lasky, L. A. Science, 1992, 258, 964. C) Rice, G. E.; Bevilacqua, M. P.; Science 1989, 246-1303. D) Bevilacqua, M. P.; Stengeling, S.; Gimbrone, M. A.; Seed, J. B. Science 1989, 243, 1160.
6. a) Phillips, M. L.; E. Nudelman, F. C.; Gaeta, A.; Perez, M.; Singhal, A. K.; Hakomori, S. I. Science 1990, 250, 1130; b) G. Waltz, A.; Arufto, W.; Kolanis, M.; Bevilacqua; B. Seed, Science 1990, 250, 1132. C) Lewe, J. B.; Stoolman, L. M. Cell.1990, 63, 475.
7. a) Ichikawa, Y.; Shen, G. J.; Wong, C. H. J. Am. Chem. Soc. 1991, 113, 4698-4700. B) Ichikawa, Y.; C. Liu, J. L.; Shen, G. J.; Wong, C. H. J. Am. Chem. Soc. 1991, 113,6300-6302. C) Ichikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G. J.; Junceda, E. G.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C. H. J. Am.Chem. Soc. 1992, 114, 9283-9298.
8. Molean, J. Am. J. Physiol. 1916, 41, 250-257.
9. Capila, I.; Lindhardt, R. J. Angew. Chem. Int. Ed. 2002, 1, 390-412.
10. a) Bockel, C. A. A. van; Petitou, M. Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1690; b) Petitou, M.; Bockel, C. A. A. van Angew. Chem. Int. Ed. 2004, 43, 3118-3133.
11. Drak, J; Iwasawa, N; Danishefsky, S.J; Crothers, D.M. Proc.Natl.Acad.Sci.USA 1991, 88, 7464.
12. Ge, M; Chen, Z; Kahne, D. Science 1999, 284, 507.
13. Nicolaou, K. C.; Mitchell, H. J.; Suzuki, H.; Rodrìguez, R. M.; Baudoin, O.; Fylaktakidou, K.C. Angew. Chem. Int. Ed. 1999, 38, 3334.
14.金城.糖生物学:基因组学和蛋白质组学的延伸,世界科技研究与发展, 2000, 23(2), 31。
15. Zhang Z.; Ollmann I. R.; Ye X. S.; Wischnat R.; Baasov T.; Wong C. H. J. Am. Chem. Soc.1999, 121, 734.
16. Plante O. J.; Palmacci E. R.; Seeberger P. H. Science. 2001, 291, 1523.
17. Bronislaw L. Slomiany, Varahabhotla L. N. Murty, Yun H. Liau et al, Animal Glycoglycerolipids, Prog. Lipid Res., 1987, 26 , 29-51.
18. Sweeley, CC.; Siddiqui, B. Chemistry of mammalian glycolipids. In: Horowitz MI, Pigman W, eds. The Glycoconjugates. New York: Academic Press, 1977, Vol I. 459-540.
19.陈惠黎,王克夷,糖复合物的结构和功能,第一版,上海:上海医科大学出版社, 1997, 164-209.
20. William Curatolo, The physical properties of glycolipids, Biochibica et Biophysica Acta, 1987, 906, 111-136.
21. William Curatolo, Glycolipid function, Biochibica et Biophysica Acta, 1987, 906, 136-160.
22. Teruyuki Sakai, Yasuhiko Koezuka, Glycolipid derivatives as therapeutic agents, Exp. Opin. Ther. Patents, 1999, 9(7), 917-930.
23. Zeller CB and Marchase RB.Am J Physiol, 1992; 262; C1341.
24.吴谷盛.神经节苷脂在神经组织中的功能与作用机理.细胞生物化学杂志,1986,823.
25.唐向东,佟振清,杨文俊,生命的化学,1994; 14(3); 25-27.
26. Geisler Fh, Dorsey FC and Coleman WP.N Engl Med, 1991; 324; 1829.
27.小仓治夫,古火田公夫.シアル酸诱导体の合成.有机合成化学会志1984;42:536
28. M. J. Horowitz, W. Pigman, the Glycoconjugates Academic Press, New York, 1978, vol I and II.
29. Schauer, R.; Kamerling, J. P. In Glycoproteins II; Montreuil, J.,Vliegenthart, J. F. G., Schachter, H., Eds.; Elsevier: Amsterdam, 1997; pp 243-402.
30. Biology of the Sialic Acids; Rosenberg, A., Ed.; Plenum Press: New York, 1995.
31. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131-234.
32. Varki, A. Glycobiology 1993, 3, 97-130.
33. Sialic Acids: Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer-Verlag: Wein, 1982; Vol. 10.
34. A. Varki, Glycobiology 1993, 3, 97.
35. M. Von Itzstein; W. Y. Wu; G. B. Kok; etal. Nature, 1993, 363, 418-423.
36. C. U. Kim; W. Lew; M. A. Willians; etal. J. Am. Chem. Soc. 1997, 119, 681-690.
37. Taki, T.; Hirabayashi, Y.; Ishikawa, H.; Ando, S.; Kon, K.; Tanaka, Y.; Matsumoto, M. J. Biol. Chem. 1986, 261, 3075-3078.
38. Hirabayashi, Y.; Hamaoka, A.; Matsumoto, M.; Matsubara, T.; Tagawa, M.; Wakabayashi, S.; Taniguchi, M. J. Biol. Chem. 1985, 260, 13328-13333.
39. Bremer, E. G.; Hakomori, S.; Bowen-Pope, D. F.; Ralnes, E.; Ross, R. J. Biol. Chem. 1984, 259, 6818-6825.
40. For a review see: Gangliosides and Cancer; Oettgen, H. F., ed.; VCH, N.Y., 1989.
41. Portoukalian, J.; Zwinglstein, G.; Dore, J.-F.; Borgion, J. J. Biochem. 1976, 56, 1285.
42. Yamakawa, T.; Suzuki, S. J. Biochem. (Tokyo), 1952, 39, 383.
43. a) Hanai, N.; Nores, G. A.; MacLeod, C.; Torres-Mendez, C. R.; Hakomori, S. J. Biol. Chem.` 1988, 263, 10915-10921. b) Bremer, E.; Schlessinger, J.; Hakomori, S. J. Bio. Chem. 1986, 261, 2434.
44. Roy, R. Design and Syntheses of Glycoconjugates. In Modem Methods in Carbohydrate Synthesis; Khan, S. H., O'Neil, R., Eds.; Harwood Academic, Amsterdam, 1996, pp. 378-402.
45. a) Gamian, A.; Chomik, M.; Laferri~re, C. A.; Roy, R. Can. J. Microbiol. 1991, 37, 233-237; b) Roy, R.; Andersson, F.O.; Harms, G.; Kelm, S.; Schauer, R. Angew. Chem` Int. Ed. EngL 1992, 31, 1478-1481; c) Spaltenstein, A.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 686-687.
46. a) Sugimoto, M.; Ogawa, T. Glycoconjugate J. 1985, 2, 5-9; b) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1989, 188, 71-80; c) Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25; d) LOnn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116; e) Ray, A. K.; Nilsson, U.; Magnusson, G. J. Am. Chem. Soc. 1992, 114, 2256-2257; f) Ercegovic, T.; Magnusson, G. J. Chem` Soc. Chelr. Commun. 1994, 831-832; g) Lui, K. K.-C.; Danishefsky, F. J. Am. Chem. Soc. 1993, 115, 4933-4934; h) Ito, Y.; Paulson, J. C. J. Am. Chem. Soc. 1993, 115, 1603-1605; i) Ercegovic, T.; Magnusson, G. J. Org. Chem. 1995, 60, 3378-3384.
47. a) A. Gottschalk, Nature 1951, 167, 845; b) A. Gottschalk, Nature 1955, 176, 881.
48. M. J. Horowitz, W. Pigman, the Glycoconjugates Academic Press, New York, 1978, vol I and II.
49. Schauer, R. Sialic Acids; Chemistry, Metabolism and Function Vol. 10, Springer-Verlag, NewYork City, 1982.
50. a) Okamoto, K.; Goto, T. Tetrahedron 1990, 46, 5835-5857; b) M. P. Deninno, Synthesis. 1991, 583; c) G.-J. Boons, A. V. Demchenko, Chem. Rev. 2000, 100, 4539.
51. Sina?, P. Pure Appl. Chem. 1991, 63, 519-528.
52. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
53. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173-200.
54. Boons, G. J. Tetrahedron 1996, 52, 1095-1121.
55. Whitfield, D. M.; Douglas, S. P. Glycoconjugate J. 1996, 13, 5-17.
56. Veeneman, G. H. In Carbohydrate Chemistry; Boons, G., Ed.; Blackie Academic & Professional: London, 1998; pp 98-174.
57. Schmidt, R. R.; Castro-Palomino, J. C.; Retz, O. Pure Appl. Chem. 1999, 71, 729-744.
58. DeNinno, M. P. Synthesis 1991, 583-593.
59. a) W. Koenigs, E. Knorr, Chem. Ber. 1901, 34, 957; b) K. Igarashi, Adv. Carbohydr. Chem. Biochem. 1977, 34, 243; c) B. Helferich, Zirner, J. Chem. Ber. 1962, 95, 2604.
60. H. Paulsen, Angew. Chem. Int. Ed. Eng. 1982, 21, 155.
61. a) R. R. Schmidt, M. Reichrath, Angew. Chem. Int. Engl. 1979, 18, 466; b) F. Paquet, P. Sin?y, J. Am. Chem .Soc. 1984, 106, 8313; c) D. Crich, T. Ritchie, J. Chem. Soc., Chem. Commun. 1988, 1461.
62. Ito, Y.; Gaudino, J. J.; Paulson, J. C. Pure Appl. Chem. 1993, 65, 753-762.
63. von Itzstein, M.; Thomson, R. J. Topics Curr. Chem. 1997, 186, 119-170.
64. Hasegawa, A.; Okhi, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res., 1991, 212, 277.
65. Hasegawa, A.; Nagahama, T.; Okhi, H.; Hotta, K.; Ishida, H.; Kiso, M. J. Carbohydr. Chem., 1991, 10, 493-498.
66. Cao, S.; Meunier, S.; Andersson, F.; Letellier, M.; Roy, R. Tetrahedron Asymmertry, 1994, 5, 2303.
67. Roy, R. Topics Curr. Chem. 1997, 187, 241-274.
68. Nicolaou, K. C.; Bockovich, N. J. In Bioorganic Chemistry: Carbohydrates; Hecht, S., Ed.; Oxford University Press: New York, Oxford, 1999; pp 134-173.
69. Hasegawa, A. In Synthetic Oligosaccharides; Kovac, P, Ed.; 1994; Vol. 560, pp 184-197.
70. Schmidt, R. R. In Synthetic Oligosaccharides; Kovac, P., Ed.; 1994; Vol. 560, pp 276-296.
71. Fraser-Reid, B.; Madsen, R.; Campbell, A. S.; Roberts, C. S.; Merritt, R. J. In Bioorganic Chemistry: Carbohydrates; Hecht, S., Ed.; Oxford University Press: New York, Oxford, 1999; pp 89-133.
72. Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
73. Kanie, O.; Ogawa, T.; Ito, Y. J. Synth. Org. Chem., Jpn. 1998, 56, 952-962.
74. a) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1988, 184, C1-C4; b) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1989, 188, 71-80; c) Murase, T.; Kameyama, A.; Kartha, K. P. R.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1989, 8, 265-283; d) Kanie, O.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1988, 7, 501-506.
75. a) Ito, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1998, 306, 581-585; b) Ehara, T.; Kameyama, A.; Yamada, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1996, 281, 237-252. c) Roy, R.; Andersson, F. O.; Letellier, M. Tetrahedron Lett. 1992, 33, 6053-6056. d) Kiso, M.; Ando, K.; Inagaki, H.; Ishida, H.; Hasegawa, A. Carbohydr. Res. 1995, 272, 159-178.
76. a) Ding, Y.; Fukuda, M.; Hindsgaul, O. Bioorg. Med. Chem. Lett. 1998, 8, 1903-1908; b) Ando, H.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1999, 18, 603-607; c) Ando, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1997, 300, 207-217.
77. a)Liebe, B.; Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778; b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. O.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616-1634; c) Cao, S.; Meunier, S. J.; Andersson, F. O.; Letellier, M.; Roy, R. Tetrahedron: Asymmetry 1994, 5, 2303-2312; d) Ellervick, U.; Magnusson, G. J. Org. Chem. 1998, 63, 9314-9322; e) Ellervick, U.; Grundberg, H.; Magnusson, G. J. Org. Chem. 1998, 63, 9323-9338; f) Salvatore, B. A.; Prestegard, J. H. Tetrahedron Lett. 1998, 39, 9319-9322; g) Tietze, L. F.; Janssen, C. O.; Gewert, J. A. Eur. J. Org. Chem. 1998, 1887-1894.
78. a) A. Marra, P. Sina?, Carbohydr. Res. 1990, 195, 303; b) W. Birberg, H, L?nn, Tetrahedron Lett. 1991, 32, 7453; c) V. Martichonok, G. Whitesides, J. Org. Chem. 1996, 61, 1702; d) J.-R. Pougny, P. Sina?, Tetrahedron Lett. 1976, 45, 4073; e) A. J. Raccliffe, B. Fraser-Reid, J. Chem. Soc., Perkin Trans I 1990, 747; f) I. Braccini, C. Derouet, J. Esnault, C. Herre du Penhoat, J.-M. Mallet, V. Michon, P. Sina?, Carbohydr. Res. 1993, 246, 23.
79. H. Kondo, Y. Ichikawa, C.-H. Wong, J. Am. Chem. Soc. 1992, 114, 8748-8750.
80. T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123-6126.
81. Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25.
82. a) Singh, K.; Fernandez-Mayoralas, A.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775-776; b) Coteron, J. M.; Singh, K.; Asensio, J. L.; Domingues-Dalda, M.; Fernandez-Mayoralis, A.; Jimenez-Barbero, J.; Martin-Lomas, M. J. Org. Chem. 1995, 60, 1502-1519.
83. a) Schmidt, R. R. In Synthetic Oligosaccharides; Kovac, P., Ed.; 1994; Vol. 560, pp 276-296; b) Greilich, U.; Brescello, R.; Jung, K. H.; Schmidt, R. R. Liebigs. Ann. 1996, 663-672.
84. M. Adinolfi, G. Barone, A. Iadonisi, M. Schiattarella, Synlett 2002, 269-270.
85. a) B. Yu, H. Tao, Tetrahedron lett. 2001, 42, 2405-2407; b) B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099-9102; c) S. Cai, B. Yu, Org. Lett. 2003, 21, 3827-3830.
86. a) K. Uneyama, J. Fluo. Chem. 1999, 97, 11; b) K. Tamura, H. Mizukami, K. Maeda, H. Watananbe, K. Uneyama, J. Org. Chem. 1993, 58, 32-35.
87. R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.
88. R. R. Schmidt, Pure & Appl. Chem. 1989, 61, 1257-1270.
89. a) R. R. Schmidt, H. Gaden, H. Jatzke, Tetrahedron Lett. 1990, 31, 327-330; b) R. R. Schmidt, J. Michel, M. Roos, Lieb. Ann. Chem. 1984, 1343-1357.
90.陶厚朝硕士论文,中国科学院上海有机所,2002.
91. L. A. Mulard, C. Costachel, P. J. Sansonetti, J. Carbohydr. Chem. 2000, 19, 849-877.
92. a) R. R. Schmidt, W. Kinay, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21; b) R. R. Schmidt, K.-J. Jung, In Preparative Carbohydrate Chemistry, S. Hanessian Ed., Marcel Dekker: New York, 1997, p 283.
93. a) Takahashi, T.; Tsukamoto, H.; Yamada, H.; Tetrahedron Lett. 1997, 38, 8223; b) Ye, X.; Huang, X.; Wong, C.H. Chem. Comm., 2001, 974-975; c) Haberman, J.M,; Gin, D.Y. Org. Let. 2001, 3(11), 1665-1668; d) Haberman, J.M,; Gin, D.Y. Org. Let. 2003, 5(14), 2539-2541; e) Koketsu, M.; Balagurunathan, K.; Linhard, R.J. Org. Let., 2000, 2, 3361.
94. a) Okamoto, k.; Knodo, T.; Goto, T. Tetrahadron Lett., 1986, 27, 5233; b) Okamoto, k.; Knodo, T.; Goto, T.` Tetrahadron Lett., 1987, 28, 5919; c) Okamoto, k.; Knodo, T.; Goto, T. Bull. Chem. Soc. Jpn., 1987, 60, 637.
95. a) Castro-Palomino, J. C.; Tsvetkov, Y. E.; Schmidt, R. R. J. Am. Chem. Soc. 1998, 120, 5434-5440; b) Castro-Palomino, J. C.; Tsvetkov, Y. E.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 6837-6840.
96. a) Ito, Y.; Ogawa, T. Tetrahadron Lett., 1988, 29, 3987; b) Kononov, L. O.; Ito, Y.; Ogawa, T. Tetrahadron Lett., 1997, 38, 1599.
97. a) Ercegovic, T.; Magnusson, G. J. J. Org. Chem., 1995, 60, 3378; b) Hossain, N.; Magnusson, G. J. Tetrahadron Lett., 1999, 40, 2217; c) Martinchonok, V.; Whitesidex, G. M. J. Am. Chem. Soc., 1996, 118, 8187;
98. Ye, D.; Liu, W.; Zhang, D.; Feng, E.; Jiang, H.; Liu, H. J. Org. Chem. 2009, 74, 1733-1735;
99. a) Demchenko, A. V.; Boons, G.-J. Tetrahadron Lett., 1998, 39, 3065; b) Demchenko, A. V.; Boons, G.-J. Chem. Eur. J., 1999, 5, 1278; c) De Meo, C.; Demchenko, A. V.; Boons, G.-J. J. Org. Chem., 2001, 66, 5490;
100. Meo, C. D.; Priyadarshani, U. Carbohydr. Res. 2008, 343, 1540-1552;
101. Crich, D.; Li, W.; J. Org. Chem. 2007, 72, 2387-2391;
102. M. Sugimoto and T. Ogawa, Glycoconjugate J., 2 (1985) 5-9.
103. J.F.G. Vliegenthart and J.P. Karnerling, in R. Schauer, (Ed.), Sialic Acids-Chemistry, Metabolism and Function, Cell Biology Monographs, Vol. 10, Springer, New York, 1982, pp 59-76.
104. (a) R.R. Schmidt and E. Riicker, Tetrahedron Lett., 1980, 211, 421-1424; (b) R.R. Schmidt and J. Michel, J. Carbohydr. Chem., 1985, 4, 141-169; (c) R.R. Schmidt, M. Behrendt, and A. Toepfer, Synlett, 1990, 694-696; (d) R.R. Schmidt, in H. Ogura, A. Hasegawa, and T. Suami (Eds.), Carbohydrates- Synthetic Methods and Applications in Medicinal Chemistry., Kodansha, Tokyo, 1992, 66-88.
105. A. Hasegawa, K. Adachi, M. Yoshida, and M. Kiso, Carbohydr. Res., 1992, 230, 273-288.
106. H. Prabhanjan, K. Aoyama, M. Kiso, and A. Hasegawa, Carbohydr. Res., 1992, 233, 87-99.
107. a) A. Marra and P. Sinai, Carbohydr. Res., 1989, 187, 35-42; b) A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, and M. Kiso, Carbohydr. Res., 1991, 212, 277-281; c) A. Hasegawa, K. Adachi, M. Yoshida, and M. Kiso, Carbohydr. Res., 1992, 230, 257-272.
108. T. Kondo, H. Abe, and T. Goto, Chem. Lett., (1988) 1657-1660.
109. a) Y. Ito and T. Ogawa, Tetrahedron Lett., 28 (1987) 6221-6224; b) Y. Ito and T. Ogawa,Tetrahedron, 46 (1990) 89-102.
110. K. Okamoto, T. Kondo, and T. Goto, Bull. Chem. Soc. Jpn., 60 (1987) 631-636.
111. a) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron Lett., 27 (1986) 5229-5232; b) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron Lett., 27 (1986) 5233-5236; c) K. Okamoto, T. Kondo, and T. Goto, Chem. Lett., (1986) 1449-1452; d) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 43 (1987) 5909-5918; e) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 43 (1987) 5919-5928; f) K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 44 (1988) 1291-1298; g) K. Okamoto and T. Goto, Tetrahedron, 46 (1990) 5835-5857.
112. a) Uneyama, K. J. Fluo. Chem. 1999, 97, 11; b) Tamura, K.; Mizukami, H.; Maeda, K.; Watananbe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32-35.
113.阮晓红论文,中国海洋大学
114. Adinolfi, M.; Iadonisi, A.; Ravida, A.; Schiattarella, M. J. Org. Chem. 2005, 70, 5316-5319.
115.蔡苏棠论文,中国科学院上海有机所
116. Boons, G. J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539-4565;
117. Shull, B. K.; Wu, Z.; Koreeda, M. J. Carbohydr. Chem. 1996, 15, 955;
118. Li, Y.; Wu, Y. Liebigs Ann. Chem. 1996, 2079;
119. Du, W.; Gervay-Hague, J. Organic Lett. 2005, 7, 2063-2065;
120. Koerner Jr. T. A. W.; Prestegard, J. H.; Demou, P. C.; Yu, R. K. Biochemistry 1983, 22, 2676-2687;
121. Hotha, S.; Kashyap, S. J.Am. Chem. Soc. 2006, 128, 9620-9621;
122. Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604-3608;
123. (a): Sashida, H.; Kawamukai, A. J. Heterocycl. Chem. 1998, 35, 165-167; (b): Bytschkov, I.; Siebeneicher, H.l Doye, S. Eur. J. Org. Chem. 2003, 68, 2888-2902.
124. Wang, P.; Kim, Y.; Navarro-Villalobos, M.; Rohde, R. D.; Gin, D. Y. J. Am. Chem. Soc. 2005, 127, 3256-3257.
125. Al-Sa’Ady, A. K.; McAuliffe, C. A.; Parish, R. V.; Sandeank, J. A. Inorg. Synth. 1985, 191-194;
126. Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem. 1988, 7, 453.
127. Nieto-Oberhuber, C.; Perez-Galan, P.; Herrero-Gomez, E.; Lauterbach, T.; Rodriguez, C.;Lopez, S.; Bour, C.; Rosellon, A.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269-279.
128. Meo, C. D.; Farris, M.; Ginder, N.; Gulley, B.; Priyadarshani, U.; Woods, M. Eur. J. Org. Chem. 2008, 3673-3677.
129. Beaulieu, F.; Ouellet, C.; R.uediger, E. H.; Belema, M. etal. Biooraganic Med. Chem. Lett. 2007, 17, 1233-1237;
130. Okamoto R.; Souma, S.; Kajihara, Y. J. Org. Chem. 2008, 73, 3460-3466;
131. Meo. C. D.; Priyadarshani, U. Carbohydr. Res. 2008, 343, 1540-1552.