Collect. Czech. Chem. Commun.
1989, 54, 2784-2794
https://doi.org/10.1135/cccc19892784
An alternative synthesis of O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine
Miroslav Ledvina, Jiří Farkaš, Jaroslav Zajíček, Jan Ježek and Milan Zaoral
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
Abstract
Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (VIII) with benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)-methyl-α-D-glucopyranoside (IV) afforded benzyl 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IX) which, after deprotection, was converted into the acid XI. Condensation of acid XI with L-α-aminobutanoyl-D-isoglutamine benzyl ester and subsequent hydrogenolysis of the product XIII furnished compound XIV. Benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IV) was prepared by partial benzoylation of benzyl 2-acetamido-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (III) with benzoyl cyanide.
