α-glucosaminide synthesis:: exercising stereocontrol at C1 or C2 via torsional effects or DeShong nucleophiles

被引：13

作者：

Anilkumar, G ^{[1
]}

Nair, LG ^{[1
]}

Olsson, L ^{[1
]}

Daniels, JK ^{[1
]}

Fraser-Reid, B ^{[1
]}

机构：

[1] Nat Prod & Glycotechnol Res Inst Inc, Durham, NC 27707 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 40期

基金：

美国国家卫生研究院;

关键词：

hypervalent silicon azido nucleophiles; n-pentenyl glycosides; n-pentenyl orthoesters;

D O I：

10.1016/S0040-4039(00)01329-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of alpha-glucosaminides may be carried out by installing synthons for the cis-related C1 and C2 functionalities in either order. When the C2 azide is installed first, cc-glycosidation can be induced by using a 4,6-O-benzylidene ring to provide torsional control of anomeric selectivity. In the alternative option, the C1 linkage can be established by use of an n-pentenyl-manno-1,2-orthoester, the C2-oxygen of the resulting alpha-mannoside being replaced with inversion by use of DeShong's hypervalent silicon azide. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7605 / 7608

页数：4

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