Abstract
Abstract Aryl and alkyl S-glycosides and sulfones are ideal precursors of three classes of reactive intermediates : anomeric carbenium, anion, and radical, and thus play a remarkable role in carbohydrate chemistry of the anomeric carbon atom. Reported reactions will include: - A conceptually novel glycosylation reaction based on the activation of thioglycosides by a one electron -transfer reagent - Uses of a novel class of glycosyl donors: anomeric S-xanthates of 2-azido sugars. - Selective synthesis of α and β C-glycosides using anomeric reductive lithiation or reductive samariation of phenyl S-glycosides or sulfones. - Convenient synthesis of substituted pyranoid glycals - Expeditious synthesis of C-disaccharides by Sml2 induced intramolecular coupling reaction of tethered glycosyl phenyl sulfone and exomethylene sugar.
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