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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 by Baráth, Marek; Petrušová, Mária; Hirsch, Ján; Petruš, Ladislav is a Chemistry article available to read on EtoBox.

What is 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 about?

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.

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Author

Baráth, Marek; Petrušová, Mária; Hirsch, Ján; Petruš, Ladislav

Publisher

UOCHB; Institute of Organic Chemistry & Biochemistry, Academy of Sciences of the Czech Republic; Akademie Ved Ceske Republiky; Institute of Organic Chemistry & Biochemistry (ISSN 0010-0765)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)