Organic & biomolecular chemistry

1, 2-cis Alkyl glycosides: straightforward glycosylation from unprotected 1-thioglycosyl donors

B Meng, Z Zhu, DC Baker

Index: Meng, Bo; Zhu, Zhenqian; Baker, David C. Organic and Biomolecular Chemistry, 2014 , vol. 12, # 28 p. 5182 - 5191

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Citation Number: 7

Abstract

A 1, 2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1, 2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)–ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small ...