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

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...

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Bibliographic Details
Published in:Organic letters 2003-10, Vol.5 (22), p.4219-4222
Main Authors: Lam, Son N, Gervay-Hague, Jacquelyn
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Deoxy Sugars - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Hydrocarbons, Aromatic - chemistry
Hydrocarbons, Iodinated - chemistry
Isomerism
Magnetic Resonance Spectroscopy
Molecular Structure
Trimethylsilyl Compounds - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035705v