Synthesis of a Precursor of a Lipid A Mimic

Baráth, M., Petrušová, M., Bystrický, S., Křen, V. and Petruš, L. Synthesis of a Precursor of a Lipid A Mimic Chemical Papers, Vol.57, No. 2, 2003, 125-130

Document type: Článok z časopisu / Journal Article
Collection: Chemical papers  
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Author(s) Baráth, M.
Petrušová, M.
Bystrický, S.
Křen, V.
Petruš, L.
Title Synthesis of a Precursor of a Lipid A Mimic
Journal name Chemical Papers
Publication date 2003
Year available 2003
Volume number 57
Issue number 2
ISSN 0366-6352
Start page 125
End page 130
Place of publication Poland
Publisher Versita
Collection year 2003
Language english
Subject 250000 Chemical Sciences
250300 Organic Chemistry
Abstract/Summary The lipid A mimic precursor, methyl 6-O-(4,6-di-O-acetyl-2,3-di-O-tetradecyl-β-D-glucopyranosyl)- 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-glucopyranoside having the original O- and N-acyl substitution at the atoms C-2, C-3, C-2, and C-3 of the carbohydrate skeleton mimicked by ether linkages was synthesized by coupling the respective monosaccharide glycosyl bromide and 6-hydroxy nucleophile in heptane—chloroform solution promoted with silver oxide. For the 2,3-di-O-alkylation of both monosaccharide precursors the efficiency of potassium tert-butoxide/tert-butanol/tetradecyl bromide for the etherification was evaluated.
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