Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.
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 - 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.
Department of Chemistry and School for Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, USA.
Vishwanath
V
Gaitonde
Steven J
SJ
Sucheck