[alpha]-Selective synthesis of 2-deoxy-glycosides and disaccharides

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°C to form glycosides, glycoconjugate...

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Published inJournal of carbohydrate chemistry Vol. 37; no. 3; p. 128
Main Authors Yang, Guofang, Luo, Xiaosheng, Guo, Hong, Wang, Qingbing, Zhou, Jiafen, Huang, Tianyun, Tang, Jie, Shan, Junjie, Zhang, Jianbo
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis Ltd 01.03.2018
Subjects
Catalysis
Chemical synthesis
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Summary: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°C to form glycosides, glycoconjugates, and disaccharides with excellent α-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.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2018.1439498