Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion

被引：46

作者：

Cox, Daniel J. ^{[2
]}

Fairbanks, Antony J. ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 8140, New Zealand

[2] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 6-8期

基金：

英国工程与自然科学研究理事会;

关键词：

INTRAMOLECULAR AGLYCON DELIVERY; STEREOCONTROLLED SYNTHESIS; BETA-MANNOSYLATION; STEREOSPECIFIC SYNTHESIS; 1,2-CIS GLYCOSIDES; GLYCOSYLATION; IAD; MANNOPYRANOSIDES; OLIGOSACCHARIDES; THIOGLYCOSIDES;

D O I：

10.1016/j.tetasy.2009.02.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective alpha-glucosylation of a trichloroacetimidate donor: increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：773 / 780

页数：8

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