ELECTROPHISIC AZIDATION OF 2-DEOXY-ALDONO-1,5-LACTONES - AN ALTERNATIVE ROUTE TO 2-AZIDO-2-DEOXY-ALDOPYRANOSES

被引：13

作者：

DUPRADEAU, FY

HAKOMORI, SI

TOYOKUNI, T

机构：

[1] BIOMEMBRANE INST, SEATTLE, WA 98119 USA

[2] UNIV WASHINGTON, DEPT PATHOBIOL, SEATTLE, WA 98195 USA

[3] UNIV WASHINGTON, DEPT CHEM, SEATTLE, WA 98195 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 02期

关键词：

D O I：

10.1039/c39950000221

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electrophilic azidation of tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 3 with triisopropylphenylsulfonyl azide, followed by selective reduction with diisobutylaluminium hydride, yielded tri-O-benzyl-2-azido-2-deoxy-D-galactopyranose 5 as the sole product in 80% yield, while the same sequence of reactions with the 2-deoxy-glucono-1,5-lactone derivative 8 afforded only tri-O-benzyl-2-azido-2-deoxy-D-mannopyranose 10 in 65% yield.

引用

页码：221 / 222

页数：2

共 29 条

[1]

BERNASCONI C, 1979, B SOC CHIM FR II-CH, P332

[2] ADDITION OF HALOGENOAZIDES TO GLYCALS [J].