Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid:: Stereoselective synthesis of glycosides and 2-deoxyglycosides

被引：50

作者：

Poláková, M ^{[1
]}

Pitt, N ^{[1
]}

Tosin, M ^{[1
]}

Murphy, P ^{[1
]}

机构：

[1] Univ Coll Dublin, Conway Inst Biomol & Biomed Res, Dept Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 19期

关键词：

carbohydrates; glucuronic acid; glycosides; glycosylation; stereoselective synthesis;

D O I：

10.1002/anie.200353196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2-trans- and 1,2-cis-(deoxy)glycosides in moderate to excellent yields.

引用

页码：2518 / 2521

页数：4

共 29 条

[1] THE SYNTHESIS OF ARYL-D-GLUCOPYRANOSIDURONIC ACIDS [J].