A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor

被引：162

作者：

Burkart, MD

Zhang, ZY

Hung, SC

Wong, CH

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

[2] Scripps Res Inst, SKAGGS INST CHEM BIOL, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 49期

关键词：

D O I：

10.1021/ja9723904

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper describes a high-yield, one-step synthesis of 2-deoxy-2-fluoro sugars and their glycosides from glycals using the available electrophilic fluorination reagent 1-chloromethyl-4-fluoro-1,4-diazoniabicyclol[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) in the presence of a nucleophile. The method was further expanded to the synthesis of glycosyl fluorides and glycosides from anomeric hydroxy or thioglycoside derivatives.

引用

页码：11743 / 11746

页数：4

共 36 条

[1] N-HALOGENO COMPOUNDS .14. TRANSFER FLUORINATION OF QUINUCLIDINE USING F-TEDA-BF4 (SELECTOR(TM) REAGENT) - LABORATORY SYNTHESIS OF N-FLUOROQUINUCLIDINIUM SALTS NOT REQUIRING THE USE OF ELEMENTAL FLUORINE [J].