Oxidation of carbohydrates with dimethy sulfoxide containing phosphorus pentoxide. II. Isolation of permethylated dicarbonyl sugar derivatives from polysaccharides.

Abstract

Oxidation of methyl trimethyl glucopyranosides which were obtained by methanolysis of permethylated cellulose, laminarin, and dextran, was performed with dimethyl sulfoxide (DMSO)-phosphorus pentoxide to afford the corresponding ulose derivatives, methyl 2, 3, 6-tri-O-methyl-D-xylo-hexopyranosid-4-ulose, methyl 2, 4, 6-tri-O-methyl-D-ribo-hexopyranosid-3-ulose, and methyl 2, 3, 4-tri-O-methyl-D-gluco-hexodialdo-1, 5-pyranoside, respectively, in good or moderate yields. As a new type of derivatives for the linkage analysis of polysaccharides the chromatographic and spectrometric properties of 2, 4-dinitrophenylhydrazone of the ulose derivatives were investigated.