An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

被引：15

作者：

Azumaya, I ^{[1
]}

Niwa, T ^{[1
]}

Kotani, M ^{[1
]}

Iimori, T ^{[1
]}

Ikegami, S ^{[1
]}

机构：

[1] Teikyo Univ, Fac Pharmaceut Sci, Kanagawa 1990195, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 25期

关键词：

carbonates; decarboxylation; glycosidation; neighbouring group effects;

D O I：

10.1016/S0040-4039(99)00843-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4683 / 4686

页数：4

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