Journal of Carbohydrate Chemistry 2013-01-01

Synthesis of _-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.

Vishwanath Gaitonde, StevenJ Sucheck

Index: J. Carbohydr. Chem. 31(4-6) , 353-370, (2012)

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Abstract

The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected _-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. _-Glycosyl amides were then prepared in 67 - 81 % yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.