ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of a Precursor of a Lipid A Mimic

M. Baráth, M. Petrušová, S. Bystrický, V. Křen, and L. Petruš

Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava

E-mail: chemlpet@savba.sk

Received: 30 April 2002

Abstract: 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.

Full paper in Portable Document Format: 572a125.pdf

Chemical Papers 57 (2) 125–130 (2003)