Synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranosides revisited

被引：9

作者：

Saksena, R ^{[1
]}

Zhang, J ^{[1
]}

Kovác, P ^{[1
]}

机构：

[1] NIDDK, LMC, NIH, Bethesda, MD 20892 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2002年 / 21卷 / 06期

关键词：

2-(trimethylsilyl)ethyl glycosides; glycosylation; NIS/AgOTf; anomerization;

D O I：

10.1081/CAR-120016846

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：

Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding alpha-1-acetates. When beta-1-acetates were more readily available, these were converted to the alpha-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl alpha-D-mannopyranosides were obtained in excellent yields.

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收藏

页码：453 / 470

页数：18

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