[Synthesis of lipophilic muramoyldipeptide derivatives]

beta-Glycosides of N-acetylglucosamine, obtained by the oxazoline synthesis, with 2-dodecyltetradecanol-1 and 2,3-didodecyloxypropanol-1 as aglycons, were converted into muramic acids and then coupled with the dipeptide to give lipophilic glycosides of muramoyldipeptide. On the other hand, condensation of 2-dodecyltetradecanyl esters of glycine and 6-aminohexanoic acid with Boc-L-Ala-D-Glu-NH2 gave the corresponding lipophilic tripeptides, which upon coupling with alpha-benzyl-4,6-O-benzylyden-N-acetylmuramic acid yielded lipophilic esters of muramoyltripeptides. The protecting groups were removed by acid hydrolysis and hydrogenolysis.