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• W1966093423 abstract "The synthesis of the oligosaccharides β-d-Xylp-(1→2)-β-d-Manp-OMe (12), β-d-Xylp-(1→2)-[α-d-Manp-(1→6)]-β-d-Manp-OMe (17), β-d-Xylp-(1→2)-[α-d-Manp-(1→3)]- β-d-Manp-OMe (21), and β-d-Xylp-(1→2)-[α-d-Manp-(1→3)][α-d-Manp-(1→6)]-β-d-Manp-OMe (25) is described. Methyl 3-O-benzyl-4,6-O-isopropylidene-β-d-mannopyranoside (6) was prepared from the corresponding gluco-epimer (4) by oxidation, followed by stereoselective reduction. Condensation of 6 with 2,3,4-tri-O-acetyl-α-d-xylopyranosyl bromide in the presence of mercuric cyanide gave a 1:9 mixture of methyl 3-O-benzyl-4,6-O-isopropylidene-2-O-(2,3,4-tri-O-acetyl-α- (7a) and -β-d-xylopyranosyl)-β-d-mannopyranoside (7), and then 7 was converted into the acetylated disaccharide-glycoside 11. Regioselective mannosylation, with 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl bromide, at position 6 of deisopropylidenated 7 (8), using mercuric bromide as a promoter, afforded the trisaccharide-glycoside derivative 13, which was transformed into the acetylated trisaccharide-glycoside 16. The disaccharide derivative 10, obtained from 8, and the trisaccharide derivative 15, obtained from 13, were glycosylated at position 3 with O-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)trichloroacetimidate (19), using trimethylsilyl triflate as a promoter, giving rise to acetylated tri- (20) and tetra-saccharide (24) derivatives, respectively. O-Deacetylation of 11, 16, 20, and 24 gave 12, 17, 21, and 25, respectively." @default.
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• W1966093423 date "1989-02-01" @default.
• W1966093423 modified "2023-10-14" @default.
• W1966093423 title "Synthesis of four structural elements of xylose-containing carbohydrate chains from N-glycoproteins" @default.
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• W1966093423 doi "https://doi.org/10.1016/0008-6215(89)84004-2" @default.
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