A glycosylation protocol based on activation of glycosyl 2-pyridyl sulfones with samarium triflate.
[reaction--see text] Reaction of glycosyl 2-pridyl 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.
Chang
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Department of Chemistry, The Ohio State University, Columbus 43210, USA.
Lowary
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D000438:Alcohols / Q000737:chemistry; D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D012493:Samarium / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*
D000438:Alcohols; D006027:Glycosides; D008698:Mesylates; D009844:Oligosaccharides; D013450:Sulfones; D012493:Samarium; D001089:Arabinose; C012077:trifluoromethanesulfonic acid