Abstract
Four analogues of the immuunoadjuvant Muramyl dipeptide in which the D -lactic acid have been replaced by D -alanine and L -alanine have been prepared. Condensation of methyl and benzyl 2-acetamido-3-amino-4,6- 0 -benzylidene-2,3-dideoxy-α- D -glucopyranosides 3 and 4 with ethyl D , L -2-bromopropionate afforded the corresponding methyl 3-[ D - and L -1(ethoxycarbonyl)ethyl ]amino]-gluco-pyranosides 5 and 9 and the corresponding benzyl glycosides 6 and 10 . The absolute configurations of 5 , 6 , 9 and 10 were unequivocally determined by condensation of 3 and 4 with ethyl L -2-bromopropionate. Hydrolysis of 6 and 10 with KOH/MeOH, gave the benzyl 3-[[ D - and L -1-(carboxy)ethyl ]amino]-gluco-pyranosides 8 and 12 , which by condensation with L -Ala- D -isoGln-OMe and L-Ala-D-Gln-OMe followed by hydrogenolysis afforded the desired N -(2-acetamido-2,3-dideoxy-D-glucopyranosid-3-yl) derivatives of D -Ala- L -Ala- D -isoGln-OMe, D -Ala- L -Ala- D -Gln-OMe, L -Ala- L -Ala- D -isoGln-OMe, and L -Ala- L -Ala- D -Gln-OMe,
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