ALTERNATIVE SYNTHESES OF METHYLATED SUGARS .19. STEPWISE SYNTHESIS OF A METHYL BETA-XYLOTETRAOSIDE RELATED TO BRANCHED XYLANS

3,4-Di-O-acetyl-2-O-benzyl-α-d-xylopyranosyl bromide (1) reacts with methyl 2,3-anhydro-α-d-ribopyranoside (2) to afford, in high yield, methyl 2,3-anhydro-4-O- (3,4-di-O-acetyl-2-O-benzyl-β-d-xylopyranosyl)-β-d-ribopyranoside (3). Deacetylation of 3 gave 4, which reacted with 2,3,4-tri-O-acetyl-α-d-xylopyranosyl bromide to give the branched tetrasaccharide derivative 5, which, in turn, was converted by a series or conventional reactions into methyl 4-O-[3,4-di-O-(β-d-xylopyranosyl)-β-d- xylopyranosyl]-β-d-xylopyranoside. The reaction of 1 with its hydrolysis product gave 3,4-di-O-acetyl-2-O-benzyl-α-d-xylopyranosyl 3,4-di-O-acetyl-2-O-benzyl-β-d-xylopyranoside, which was also isolated after the reaction of 1 with 2. © 1979.