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.
引用
收藏
页码：453 / 470
页数：18
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