Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 28, Pages 5182-5191Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00626g
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Funding
- National Science Foundation [0906752]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [0906752] Funding Source: National Science Foundation
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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.
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