Facile Synthesis of 尾- and 伪-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

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• 作者：Shivaji A. Thadke ; Bijoyananda Mishra ; Srinivas Hotha
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：May 17, 2013
• 年：2013
• 卷：15
• 期：10
• 页码：2466-2469
• 全文大小：307K
• 年卷期：v.15,no.10(May 17, 2013)
• ISSN：1523-7052

文摘

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.