Add time:09/09/2019         Source:sciencedirect.com

Publisher SummaryThis chapter discusses the sulfonic esters of carbohydrates. Adequate methods for sulfonylation existed, and an introduced sulfonyl group provided a protecting group stable under acidic, neutral, and slightly basic conditions. Removal of the sulfonyl protecting group is known to be readily achieved by the use of sodium amalgam. The action of alkaline reagents on sulfonic esters received much attention, and the nature of the products from derivatives containing isolated or nonisolated, primary or secondary sulfonyloxy groups are known. The use of Finkelstein's reagent with sulfonic esters of sugars provided another reaction of considerable utility; the resulting replacement of primary and secondary sulfonyloxy groups with iodine in a variety of sugars is reviewed. Nucleophilic displacements of sulfonyloxy groups by reagents other than halide ions are also observed in sugar chemistry. Much of the stimulus for work on sulfonic esters of sugars has arisen from their use in the synthesis of compounds having possible chemotherapeutic activity.

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