A Glycosylation Protocol Based on Activation of Glycosyl 2-Pyridyl Sulfones with Samarium Triflate

Reaction of glycosyl 2-pyridyl sulfones (e.g., 2) with alcohols and samarium(III) triflate affords glycosides in moderate to excellent yields. Benzylated sulfones can be activated in preference to their benzoylated counterparts, and the methodology has been used to prepare di- and trisaccharides con...

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Bibliographic Details
Published in:Organic letters 2000-06, Vol.2 (11), p.1505-1508
Main Authors: Chang, Grace X, Lowary, Todd L
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Arabinose - analogs & derivatives
Arabinose - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Mesylates - chemistry
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Samarium - chemistry
Sulfones - chemistry
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Summary:Reaction of glycosyl 2-pyridyl sulfones (e.g., 2) with alcohols and samarium(III) triflate affords glycosides in moderate to excellent yields. Benzylated sulfones can be activated in preference to their benzoylated counterparts, and the methodology has been used to prepare di- and trisaccharides containing both furanose and pyranose residues. Thioglycosides do not react under these conditions, and the sulfones are inert to the N-iodosuccinimide/silver triflate promoter system commonly used to activate thioglycosides. This selectivity allowed the efficient preparation of oligosaccharides via orthogonal glycosylation protocols.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005579k