Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides

被引：40

作者：

Paul, S ^{[1
]}

Jayaraman, N ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 13期

关键词：

carbohydrates; deoxysugars; enoses; thioglycosides;

D O I：

10.1016/j.carres.2004.07.010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and alpha-anomeric 2-deoxy glycosides were obtained exclusively. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2197 / 2204

页数：8

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