Carbohydrate Research 1995-12-20

Synthesis of (1-->4)-beta-D-xylo-oligosaccharides of dp 4-10 by a blockwise approach.

K Takeo, Y Ohguchi, R Hasegawa, S Kitamura

Index: Carbohydr. Res. 278(2) , 301-13, (1995)

Full Text: HTML

Abstract

Dibutyltin oxide-mediated regioselective chloroacetylation of methyl 1-thio-beta-xylobioside, followed by treatment of the product with 4-methylbenzoyl chloride-pyridine, gave methyl 4-O-chloroacetyl-2,3-di-O-(4-methylbenzoyl)-beta-D-xylopyranosyl-(1-->4) -2.3-di - O-(4-methylbenzoyl)-1-thio-beta-D-xylopyranoside (18) in 70% yield. Coupling of 18 with benzyl alcohol afforded the disaccharide benzyl beta-glycoside, which was O-dechloroacetylated to provide methyl 2,3-di-O-(4-methylbenzoyl)-beta-D-xylopyranosyl-(1-->4)-2,3-di-O-(4- methylbenzoyl)-1-thio-beta-D-xylopyranoside (20). A homologous series of (1-->4)-beta-D-xylo-oligosaccharides from the tetra- to the deca-saccharide have been synthesized in a blockwise manner by using 20 as the glycosyl acceptor, 18, methyl 1-thio-beta-xylobioside pentaacetate, and methyl 1-thio-beta-xylotrioside heptaacetate as the glycosyl donors, and a combination of N-iodosuccinimide-silver triflate as the promoter.