C2-acetamidomannosylation.: Synthesis of 2-N-acetylamino-2-deoxy-α-D-mannopyranosides with glucal donors

被引：21

作者：

Liu, J ^{[1
]}

Di Bussolo, V ^{[1
]}

Gin, DY ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 21期

基金：

美国国家卫生研究院;

关键词：

acetamidomannosylation; glycosylation; nitrogen transfer;

D O I：

10.1016/S0040-4039(03)00871-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot C2-acetamidomannosylation reaction for the synthesis of 2-N-acetylamino-2-deoxy-alpha-D-mannopyranosides from glucals is described. Glucal donors are activated by the reagent combination of 2,8-dimethyldibenzothiophene-5-oxide (DMDBTO) and trifluoromethanesulfonic anhydride. Upon subsequent addition of N-(TMS)acetamide and an appropriate glycosyl acceptor. the corresponding C2-acetamidomaflnopyranosides are formed. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4015 / 4018

页数：4

共 34 条

[11] SYNTHESIS OF BIOLOGICALLY IMPORTANT CARBOHYDRATES .12. AMINO-SUGARS AND N-GLYCOSIDES BY OXYAMINATION OF UNSATURATED CARBOHYDRATE-DERIVATIVES [J].