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Vinyl Sulfone-modified Pyranoses and Furanoses: Synthesis and Michael Addition Reactions

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  • Chemistry
  • Chemistry


Abstract A Review on Vinyl Sulfone-modified Carbohydrates and Nucleosides Amongst various functionalized sulfones, a,b-unsaturated- or vinyl sulfones have now become generally accepted as useful intermediates in organic synthesis. The vinyl sulfones serve efficiently as both Michael acceptors and a 2p partner in cycloaddition reactions. Carbohydrates, on the other hand, are used extensively as chiral building blocks for the synthesis of various complex molecules. The preliminary requirement of such a synthesis is the functionalization of the sugar molecules at the monosaccharide level. Carbohydrates are normally modified via their sulfonates, epoxides, olefins, ketones or olefinic derivatives. Due to the high reactivities of vinyl sulfones towards a wide variety of nucleophiles, vinyl sulfone-modified carbohydrates could be used to generate an array of modified monosaccharides. Vinyl sulfone-modified carbohydrates have the potential for utilization in organic synthesis because (a) almost all carbohydrates, either in pyranose or furanose forms, could be converted to their vinyl sulfone derivatives very easily -the first step being the simple nucleophilic displacements of sulfonates or regioselective opening of epoxides by alkyl or aryl mercaptans at various positions, (b) sulfone chemistry has been exploited extensively over decades and its compatibility with a wide variety of simple and complex molecules is well established and (c) after using the vinyl sulfone moiety as a tool for functionalization, whenever necessary, the sulfone group could be removed oxidatively to generate a carbonyl group, reductively to afford a methylene group or eliminated to generate a double bond. Although vinyl sulfones have been used effectively in synthetic transformations, vinyl sulfone-modified carbohydrates are yet to be used extensively in synthetic organic chemistry. The methodologies discussed above are also applicable to the modification of the carbohydrate moieties of nucleoside

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