Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine

被引：78

作者：

Wei, P ^{[1
]}

Kerns, RJ ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo047812o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine undergoes high-yield glycosidation under mild donor activation conditions. Stereoselective formation of alpha-linked or beta-linked glycosides is dependent on reactivity of acceptor alcohols, where rate of glycosidation correlates to stereochemical outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presented.

引用

页码：4195 / 4198

页数：4

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