Collect. Czech. Chem. Commun. 1992, 57, 579-589

Synthesis of O-(2-Deoxy-2-stearoylamino-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine, a Lipophilic Disaccharide Analogue of MDP

Miroslav Ledvina, David Šaman and Jan Ježek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Partial N-deacetylation of compound II with barium hydroxide afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O,-benzyl-2-deoxy-α-D-glucopyranoside (III) in high yield. Compound III was N-acylated with stearic acid in the presence of DCC and the obtained product was converted into benzyl 2-acetamido-6-O-benzyl-3-O-carboxymethyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-α-D-glucopyranoside (VII). Coupling of compound VII with L-α-aminobutanoyl-D-isoglutamine benzyl ester followed by hydrogenolysis of the product VIII afforded compound IX.