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Dibutyltin oxide-mediated regioselective chloroacetylation of methyl 1-thio-β-xylobioside, followed by treatment of the product with 4-methylbenzoyl chloride-pyridine, gave methyl 4-O-chloroacetyl-2,3-di-O-(4-methylbenzoyl)-β-d-xylopyranosyl-(1 → 4)-2,3-di-O-(4-methylbenzoyl)-1-thio-β-d-xylopyranoside (18) in 70% yield. Coupling of 18 with benzyl alcohol afforded the disaccharide benzyl β-glycoside,...
2- and 4-Nitrophenyl β-d-xylopyranosides (4 and 5) were transformed, via dibutyltin oxide-mediated acylation, into the corresponding 2,3-di-O-benzoyl derivatives 11 and 15. Xylobiose and xylotriose were easily isolated by charcoal column chromatography from a commercially available material and converted into the di- and trisaccharide methyl 1-thio-β-glycosides 36 and 37. The 2-and 4-nitrophenyl...
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