α-Selective synthesis of 2-deoxy-glycosides and disaccharides

被引：6

作者：

Yang, Guofang ^{[1
]}

Luo, Xiaosheng ^{[1
]}

Guo, Hong ^{[1
]}

Wang, Qingbing ^{[1
]}

Zhou, Jiafen ^{[1
]}

Huang, Tianyun ^{[1
]}

Tang, Jie ^{[1
]}

Shan, Junjie ^{[2
]}

Zhang, Jianbo ^{[1
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai, Peoples R China

[2] Beijing Inst Pharmacol & Toxicol, Dept Pharmacol, Beijing, Peoples R China

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2018年 / 37卷 / 03期

基金：

上海市自然科学基金;

关键词：

2-deoxy glycosides; 2-deoxy disaccharides; TMSOTf; alpha-selective glycosylation; antitumor activity; GLYCOSYLATION; 2-DEOXY; CELLS; 2-DEOXYGLYCOSIDES; OLIGOSACCHARIDES; DIVERSIFICATION; CYTOTOXICITY; DERIVATIVES; GLYCOSIDES; EFFICIENT;

D O I：

10.1080/07328303.2018.1439498

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.

引用

页码：128 / 152

页数：25

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