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- W1973886004 abstract "The synthesis is reported of propyl 4-O-α-D-galactopyranosyl-β-D-glucopyranosiduronic acid (25), 4-O-[4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-β-D-glucopyranosyl-α-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [→4)-β-D-GlcpA-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp-(1→4)-α-D-Galp-(1→]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-O-acetyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoro-methanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38." @default.
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- W1973886004 date "1993-06-01" @default.
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- W1973886004 title "Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8" @default.
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- W1973886004 doi "https://doi.org/10.1016/s0040-4020(01)82378-4" @default.
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