Structural Influence of Sugar and Aglycon Moieties on the Acetolysis of Some Glycosylamines

Abstract

The acetolysis was applied to a novel cleavage of N-p-tolyl-β-D-glycosylamines in gluco-, galacto- and manno-configurations and their 2-acetamido-2-deoxy sugars. The results were compared with the acetolysis of furanosyl- and pyranosylnucleosides. N-Acetyl p-toluidine was isolated as crystals in up to 92% yield in the acetolysis of N-p-tolyl-β-D-glycosylamines of neutral sugars and in 1.5_??_2.0% yields in that of 2-acetamido-2-deoxy sugars. The stability of glycosylamine linkages against the acetolysis was found in the following order: pyranosyl-nucleosides (the most stable)>N-p-tolyl-β-D-glycosylamine of 2-acetamido-2-deoxy sugars>furanosylnucleosides>N-p-tolyl-β-D-glycosylamines of neutral sugars (the most unstable).