Efficient Strategy for α-Selective Glycosidation of D-Glucosamine and Its Application to the Synthesis of a Bacterial Capsular Polysaccharide Repeating Unit Containing Multiple α-Linked GlcNAc Residues

被引：38

作者：

Zhang, Yanxin ^{[1
]}

Zhang, Han ^{[1
]}

Zhao, Ying ^{[1
]}

Guo, Zhongwu ^{[2
]}

Gao, Jian ^{[1
]}

机构：

[1] Shandong Univ, Natl Glycoengn Res Ctr, Shandong Key Lab Carbohydrate Chem & Glycobiol, Qingdao 266237, Shandong, Peoples R China

[2] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; OLIGOSACCHARIDE SYNTHESIS; CARBOHYDRATE BACKBONE; GLYCOSYLATION; HEPARIN; DONORS; LIPOPOLYSACCHARIDES; STEREOSELECTIVITY; REACTIVITY; ACID;

D O I：

10.1021/acs.orglett.0c00101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient alpha-selective glycosylation method was developed for the synthesis of 2-deoxy-2-amino-n-glucosides based on synergetic alpha-directing effects of the TolSCl/AgOTf promotion system and the functional groups at the corresponding azido donor 6-O-position to exert steric beta-shielding effect or remote participation in the glycosylation reaction. Its practicability was verified with a wide range of monosaccharide glycosyl acceptors and the first, one-pot synthesis of the challenging pentasaccharide repeating unit of an Acinetobacter baumannii K47 capsular polysaccharide.

引用

页码：1520 / 1524

页数：5

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