A novel stereospecific synthesis of glycosyl cyanides from 1,2-O-sulfinyl derivatives

被引：16

作者：

Benksim, A ^{[1
]}

Beaupère, D ^{[1
]}

Wadouachi, A ^{[1
]}

机构：

[1] Univ Picardie, Lab Glucides, FRE 2779, F-80039 Amiens, France

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 22期

关键词：

D O I：

10.1021/ol0486829

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such S(N)2-type displacements at the anomeric center are stereospecific and are best performed with sodium cyanide in the presence of ytterbium triflate. Significantly, the resulting 1,2-trans-glycosyl cyanides have a free hydroxyl group at C-2 ready for further modification.

引用

页码：3913 / 3915

页数：3

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