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• W2133303096 abstract "The synthesis of a common tetrasaccharide core structure of Haemophilus influenzae lipopolysaccharides, β-d-glucopyranosyl-(1→4)-[l-glycero-α-d-manno-heptopyranosyl-(1→3)]-l-glycero-α-d-manno-heptopyranosyl-(1→5)-3-deoxy-α-d-manno-octulopyranoside, and the trisaccharide β-d-glucopyranosyl-(1→4)-[l-glycero-α-d-manno-heptopyranosyl-(1→3)]-l-glycero-α-d-manno-heptopyranoside is described. The oligosaccharides are synthesized as glycosides of a bifunctional spacer, 2-(4-aminophenyl)ethanol, to allow the subsequent formation of immunogenic glycoconjugates, which will be evaluated as well-defined glycoconjugate vaccine candidates. The syntheses of the 3,4-branched structures were accomplished using a 1,6-anhydro-l-glycero-β-d-manno-heptopyranose intermediate to diminish the steric crowding between the 3- and 4-substituent. This intermediate was effectively synthesized from a mannose precursor via a stereoselective one-carbon elongation using a Barbier reaction (which was found to be more convenient than a Grignard reaction) and anhydro bridge formation through an internal glycosylation of a 6-O-trimethylsilylated ethyl thioheptoside using NIS/TfOH as a promoter. The 3- and 4-substituent were readily introduced into the 1,6-anhydro intermediate by glycosylation reactions using thioglycosides as donors and NIS/TfOH as a promoter, a task which has not been possible using acceptors with equatorial 3,4-substituents. Acetolysis of the anhydro bridge followed by conversion into the ethyl thioglycoside afforded a trisaccharide donor, which, in NIS/TfOH-promoted couplings to the spacer and to a Kdo acceptor followed by deprotection, efficiently gave the two target compounds." @default.
• W2133303096 created "2016-06-24" @default.
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• W2133303096 date "1998-10-01" @default.
• W2133303096 modified "2023-10-16" @default.
• W2133303096 title "Synthesis of a Branched Heptose- and Kdo-Containing Common Tetrasaccharide Core Structure of <i>Haemophilus </i><i>i</i><i>nfluenzae</i> Lipopolysaccharides via a 1,6-Anhydro-<scp>l</scp>-<i>g</i><i>lycero</i>-β-<scp>d</scp>-<i>m</i><i>anno-</i>heptopyranose Intermediate" @default.
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• W2133303096 doi "https://doi.org/10.1021/jo9808573" @default.
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