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Synthesis of oligosaccharins: a chemical synthesis of propylO-β-d-galactopyranosyl-(1 → 2)-O-α-d-xylopyranosyl-(1 → 6)-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranoside

✍ Scribed by Arlette Wotovic; Jean-Claude Jacquinet; Pierre Sinay¨

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
839 KB
Volume
205
Category
Article
ISSN
0008-6215

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✦ Synopsis

Condensation of allyl 3,4-di-O-benzyl-beta-D-xylopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of silver triflate gave allyl 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-galactopyranosyl)-3,4-di-O benzyl-beta-D-xylopyranoside (7, 83%). Compound 7 was converted in five steps into 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-xylopyranosyl bromide (13), which was condensed immediately with allyl 2,3,6-tri-O-acetyl-4-O-(2,3,di-O-acetyl-beta-D-glucopyranosyl)-beta-D- glucopyranoside to give crystalline allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranosyl)- (1----2)-O-(3,4,-di-O-benzyl-alpha-D-xylopyranosyl)-(1----6)-O-(2,3,-di- O-acetyl-beta-D-glucopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-beta-D-gluco pyranoside (23, 50%). O-Deacylation of 23 followed by catalytic hydrogenolysis gave the title glycoside.

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