THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: VI. DEGRADATION OF 4-O-METHYL-D-GLUCOPYRANURONOSYL-ALDOBIURONIC ACIDS TO 2-O-(4-O-METHYL-D-GLUCOPYRANOSYL)-GYCEROLS

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Abstract
The configurations of glycosidic linkages in 4-O-methyl-D-glucopyranuronosyl-aldobiuronic acids can be determined by conversion to the derived 2-O-D-glucopyranosyl-glycerol hexamethyl ether, which is compared, by its infrared spectrum and specific rotation, with the sirupy hexamethyl ethers synthesized from 2-O-α- and 2-O-β-D-glucopyranosyl-glycerol. Thus, the configuration of 2-O-(4-O-methyl-D-glucopyranuronosyl)-D-xylose was shown to be α, since it was degraded to 2-O-α-D-glucopyranosyl-glycerol hexamethyl ether. The configuration of 4-O-(4-O-methyl-D-glucopyranuronosyl)-D-galactose was correlated with that of the former aldobiuronic acid, since both gave crystalline 2-O-α-(4-O-methyl-D-glucopyranosyl)-glycerol penta-p-nitrobenzoate.