Synthesis of hydrophobic derivatives of muramyldipeptides

Article abstract of DOI:10.1007/BF02273926

Methyl esters of the cyclohexyl-, phenethyl-, (2-naphthyl)methyl-, and 2′-(1-naphthyl)ethyl β-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine have been synthesized. The corresponding glycosides of N-acetylglucosamine were obtained by glycosylating the alcohols with the peracetate of α-glucosaminyl chloride in the presence of HgI₂, followed by deacetylation. Subsequent benzylidenation and alkylation with α-L-chloropropionic acid led to glycosylmuramic acids, the condensation of which with the dipeptide and final debenzylidenation gave the desired glycopeptides.