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

The acetolysis was applied to a novel cleavage of N-p-tolyl-β-d-glycosylamines in glucogalacto- 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: pyranosylnucleosides (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).