Add time:08/30/2019 Source:sciencedirect.com
Condensation of allyl 3,4-di-O-benzyl-β-d-xylopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-α-d-galactopyranosyl chloride in dichloromethane in the presence of silver triflate gave allyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-d-galactopyranosyl)-3,4-di-O-benzyl-β-d-xylopyranoside (7, 83%). Compound7 was converted in five steps into 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-d-galactopyranosyl)-3,4-di-O-benzyl-α-d-xylopyranosyl bromide (13), which was condensed immediately with allyl 2 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-β-d-glucopyranosyl)-β-d-glucopyranoside to give crystalline allylO-(2-O-acetyl-3,4,6-tri-O-benzyl-β-d-galactopyranosyl)- (1 → 2)-O-(3,4-di-O-benzyl- α-d-xylopyranosyl)-(1 → 6)-O-(2,3-di-O-acetyl-β-d-glucopyranosyl)-(1 → 4)-2,3,6-tri-O-acetyl-β-d-glucopyranoside (23, 50%).O-Deacetylation of23 followed by catalytic hydrogenolysis gave the title glycoside.
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