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Issue 28, 2014
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1,2-cis Alkyl glycosides: straightforward glycosylation from unprotected 1-thioglycosyl donors

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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 scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.

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

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Supplementary files

Article information


Submitted
24 Mar 2014
Accepted
03 Jun 2014
First published
03 Jun 2014

Org. Biomol. Chem., 2014,12, 5182-5191
Article type
Paper
Author version available

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

B. Meng, Z. Zhu and D. C. Baker, Org. Biomol. Chem., 2014, 12, 5182
DOI: 10.1039/C4OB00626G

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