Stereospecific synthesis of -C-glycosyl derivatives (“-C-glycosides”) of N-acetylneuraminic acid by samarium-mediated reductive desulfonylation of a glycosyl phenylsulfone

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• 作者：Du ; Yuguo ; Linhardt ; Robert J.
• 关键词：Samarium diiodide ; C-glycosyl compounds ; C-glycosides ; Phenylsulfone ; Barbier reaction ; Neu5Ac
• 刊名：Carbohydrate Research
• 出版年：1998
• 出版时间：March, 1998
• 年：1998
• 卷：308
• 期：1-2
• 页码：161-164
• 全文大小：132 K

文摘

A samarium-mediated Barbier reaction was performed to afford N-acetylneuraminic acid α-C-glycosyl compounds (“α-C-glycosides”) in excellent yield. The neuraminic acid phenyl sulfone or 2-pyridyl sulfone derivatives reacted with ketones or aldehydes resulting in the instantaneous and stereospecific formation of Neu5Ac α-C-glycosides. The phenyl and the 2-pyridyl sulfone derivatives were equally effective in this reaction. Finally, this procedure was successfully applied to the preparation of C-disaccharide, α-Neu5Ac-(2→6) Gal.