Tandem radical trifluoromethylation nucleophilic cyclization of a glucose-derived ketene dithioacetal. Synthesis of 5-deoxy-5-C-trifluoromethyl-aldurono-6,3-lactones

被引：12

作者：

Foulard, G ^{[1
]}

Brigaud, T ^{[1
]}

Portella, C ^{[1
]}

机构：

[1] Univ Reims, Fac Sci, CNRS, UMR 6519,Lab React Select & Applicat, F-51687 Reims 2, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1998年 / 91卷 / 02期

关键词：

ketene dithioacetals; radical trifluoroalkylation; glucuronolactone; iduronolactone;

D O I：

10.1016/S0022-1139(98)00223-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A diastereoisomeric mixture of 5-C-trifluoromethylated analogs of D-glucuronolactone and L-iduronolactone was synthesized in a five-step procedure from 1,2-O-isopropylidene-alpha-D-glucofuranose. The key step involves a tandem radical trifluoromethylation-nucleophilic cyclization of a ketene dithioacetal derived from 1,2-O-isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose. (C) 1998 Elsevier Science S.A. All rights reserved.

引用

页码：179 / 183

页数：5

共 30 条

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