Fluorine-Directed Glycosylation

被引：107

作者：

Bucher, Christoph ^{[1
]}

Gilmour, Ryan ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Organ Chem Lab, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 46期

关键词：

bioisosteres; conformational analysis; fluoroglycosides; organofluorine chemistry; oxonium ions; MOLECULAR MECHANICAL INVESTIGATIONS; PI-FACIAL STEREOSELECTIVITY; OXOCARBENIUM IONS; ELECTROSTATIC STABILIZATION; NUCLEOPHILIC ADDITIONS; THEORETICAL EVIDENCE; CHEMISTRY; 2-DEOXY-BETA-GLYCOSIDES; SUBSTITUENT; DONORS;

D O I：

10.1002/anie.201004467

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Everything's under control: A stabilizing fluorine electrostatic interaction has been exploited to control oxonium ion conformation in 2-fluoropyranose derivatives (see scheme). When matched with the inductive nature of the protecting groups, the glycosyl donors were found to be highly selective (2-FGluc/benzyl → β; 2-FManno/pivaloyl → α) leading to fluoro-glycostructures with excellent control over the anomeric configuration. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8724 / 8728

页数：5

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