N-glycosyl amides:: Removal of the anomeric protecting group and conversion into glycosyl donors

被引：25

作者：

Pleuss, N ^{[1
]}

Kunz, H ^{[1
]}

机构：

[1] Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 27期

关键词：

Appel reagent; glycosides; glycosyl amides; protecting groups; retro-Ritter reaction;

D O I：

10.1002/anie.200351351

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactivity upon demand: Because of their stability towards acids, bases, and many oxidizing and reducing agents, N-glycosyl amides 1 (see scheme) can be used as anomerically protected carbohydrates. The amide function can be cleaved under mild conditions with Ph3P/CBr4 and the carbohydrate activated for the synthesis of N- and O-glycosides 2. PG = protecting group.

引用

页码：3174 / 3176

页数：3

共 23 条

[1] Glycosylation-induced asymmetric synthesis:: β-amino acid esters via Mannich reactions [J].