174090-06-3

Upstream product

• 174090-05-2 methyl 2,3-di-O-benzoyl-4-O-chloroacetyl-β-D-xylopyranosyl-(1 <*> 4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside 
• 100-51-6 benzyl alcohol 
• 174090-03-0 methyl β-D-xylopyranosyl-(1 <*> 4)-1-thio-β-D-xylopyranoside 
• 173468-22-9 methyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-2,3-di-O-acetyl-1-thio-β-D-xylopyranoside 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

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

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 70percent yield.Coupling of 18 with benzyl alcohol afforded the disaccharide benzyl β-glycoside, which was O-dechloroacetylated to provide methyl 2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl-(1 -> 4)-2,3-di-O-(4-methylbenzoyl)-1-thio-β-D-xylopyranoside (20).A homologous series of (1 -> 4)-β-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-β-xylobioside pentaacetate, and methyl 1-thio-β-xylotrioside heptaacetate as the glycosyl donors, and a combination of N-iodosuccinimide-silver triflate as the promoter.Keywords: Oligosaccharides; D-xylo-; Synthesis, blockwise; Glycosidation