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

被引：26

作者：

Du, YG

Linhardt, RJ

机构：

[1] Univ Iowa, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA

[2] Univ Iowa, Dept Chem & Biochem Engn, Iowa City, IA 52242 USA

来源：

CARBOHYDRATE RESEARCH | 1998年 / 308卷 / 1-2期

关键词：

samarium diiodide; C-glycosyl compounds; C-glycosides; phenylsulfone; Barbier reaction; Neu5Ac;

D O I：

10.1016/S0008-6215(98)00054-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A samarium-mediated Barbier reaction was performed to afford N-acetylneuraminic acid alpha-C-glycosyl compounds ("alpha-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 alpha-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, alpha-Neu5Ac-(2-->6) Gal. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：161 / 164

页数：4

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