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

Carbohydrate Research
K TakeoS Kitamura

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.

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Citations

May 12, 2006·Organic & Biomolecular Chemistry·Young-Wan KimStephen G Withers
Mar 25, 2020·Organic & Biomolecular Chemistry·Cecilia RomanòMads H Clausen
Jan 11, 2018·Chemical Communications : Chem Comm·Martin Jæger PedersenMads Hartvig Clausen
Aug 10, 2017·Chemical Reviews·Christine KinnaertMads H Clausen
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Giulio FittolaniMartina Delbianco
Nov 26, 2019·The Journal of Organic Chemistry·Emilie N UnderlinRobert Madsen

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