Base-catalyzed Degradations of Carbohydrates. IX. β-Eliminations of 4-<i>O</i>-Substituted Hexopyranosiduronates

Abstract

Two methylated disaccharides, methyl [methyl 4-O-(2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl)-2,3-di-O-methyl-β-D-glucopyranosid]uronate (9) and methyl 6-O-(methyl 2,3,4-tri-O-methyl-α-D-galactopyranosyluronate)-2,3,4-tri-O-methyl-β-D-glucopyranoside (15) have been synthesized and used as model compounds for the study of the base-catalyzed β-elimination of 4-O-substituted hexopyranosiduronates without degradation of exposed reducing sugars and of the selective acid hydrolysis of hex-4-enopyranosiduronates.