Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation

被引：4

作者：

Wang, Tinghua ^{[1
]}

Singh, Yashapal ^{[1
]}

Stine, Keith J. ^{[1
]}

Demchenko, Alexei V. ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem & Biochem, One Univ Blvd, St Louis, MO 63121 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 47期

基金：

美国国家科学基金会;

关键词：

Glycosylation; Nitrate; Oligosaccharides; Carbohydrates; GLYCAN BIOMARKERS; ACTIVATION; LANTHANIDE(III); IDENTIFICATION; PLATFORM; DONORS;

D O I：

10.1002/ejoc.201801272

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.

引用

页码：6699 / 6705

页数：7