Selective cleavage of glycosidic linkages via N-nitrosoamide decomposition
Abstract
Cleavage of the glycosidic linkage occurred during the decomposition, in aqueous medium, of the N-nitroso-derivatives of two 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosides to give 3,4,6-tri-O-acetyl-2,5-anhydro-D-mannose and the aglycone; in non-aqueous medium extensive denitrosation occurred and the aglycone was retained in the products of rearrangement.