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

Gaitonde, Vishwanath; Sucheck, StevenJ.

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 cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.

ORGANIC synthesis; BENZENESULFONAMIDES; GLYCOSIDES; SACCHARIDES; AZIDES; ACETIC acid; CARBONATES

Journal of Carbohydrate Chemistry, 2012, Vol 31, Issue 4-6, p353

0732-8303

Academic Journal

10.1080/07328303.2012.663431