2-硝基硫代糖苷供体：氨基糖β-D-糖苷的通用前体。

2-nitro thioglycoside donors: versatile precursors of beta-D-glycosides of aminosugars.

作者信息

Barroca Nadine, Schmidt Richard R

机构信息

Department of Chemistry, University of Konstanz, Fach M 725, 78457 Konstanz, Germany.

出版信息

Org Lett. 2004 May 13;6(10):1551-4. doi: 10.1021/ol049729t.

DOI:10.1021/ol049729t

PMID:15128233

Abstract

2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.

摘要

2-硝基硫代糖苷可通过苯硫酚对2-硝基糖烯衍生物的迈克尔加成反应制备。在醇类存在下，这些2-硝基硫代糖苷经NIS/TMSOTf活化，能快速、干净地以良好产率和β-选择性得到所需的糖苷。硝基的还原可生成相应的2-乙酰氨基糖苷。