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- W2030440890 abstract "Compound 18 mimicking lipid A, containing D-glucose instead of D-glucosamine moieties in its gentiobiose skeleton, O -tetradecyl groups at the C-2, C-3, C-2' and C-3' instead of the ester- and amide-linked fatty acids, and O -allyl groups at the C-1α and C-4' replacing the phosphate groups, was synthesized by the Schmidt trichloroacetamidate method in a combined 8% yield of 13 steps. Allyl 4,6- O -(4-methoxybenzylidene)-α-D-glucopyranoside ( 1 ) and methyl 4,6- O -benzylidene-α-D-glucopyranoside ( 4 ) were starting materials for preparation of the respective O -alkylated and O -allylated glycosyl donor and sugar nucleophile. While boron trifluoride etherate in dichloromethane catalysed a highly preferential formation of the required β-(1→6)-glycosidic bond, α-linked lipidodisaccharide was a major product when trimethylsilyl trifluoromethanesulfonate was used as a catalyst, in both cases independently of the anomeric configuration of the starting imidate. Prolonged treatment with acid catalysts in the coupling step was exploited also for a one-pot removal of the intermediate 4- O -(4-methoxybenzyl) protection of the target mimic 18 of lipid A." @default.
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- W2030440890 date "2006-01-01" @default.
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- W2030440890 title "Synthesis of a 1α,4'-Di-O-allylated, 2,3,2',3'-Tetra-O-tetradecylated Lipid A Mimic and Its 4-O-(4-Methoxybenzyl) Precursor" @default.
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- W2030440890 doi "https://doi.org/10.1135/cccc20061532" @default.
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