Efficient Route to 2-Deoxy β-O-Aryl-D-Glycosides via Direct Displacement of Glycosyl Iodides

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Abstract

(Equation presented) The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-β-O-aryl glycosides. Direct displacement of the anomeric iodide alleviates the need to introduce temporary C-2 stereodirecting groups that require subsequent removal. The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence.

Original languageEnglish (US)
Pages (from-to)4219-4222
Number of pages4
JournalOrganic Letters
Volume5
Issue number22
DOIs
StatePublished - Oct 30 2003

ASJC Scopus subject areas

  • Molecular Medicine

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