Journal of carbohydrate chemistry

Synthesis of β-glycosyl amides from N-glycosyl dinitrobenzenesulfonamides

V Gaitonde, SJ Sucheck

Index: Gaitonde, Vishwanath; Sucheck, Steven J. Journal of Carbohydrate Chemistry, 2012 ,  vol. 31,  # 4-6  p. 353 - 370

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Citation Number: 4

Abstract

The N-glycosyl-2, 4-dinitrobenzenesulfonamides were accessed via benzoyl-protected β- 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. β-Glycosyl amides were then prepared in 67% to 81% yields by treatment of the sulfonamides with thioacetic acid and ...