Synthesis of glycosides of a muramoyldipeptide with chromone aglycones

Article abstract of DOI:10.1023/A:1017694224906

The synthesis of β-(2-methyl-3-phenylchromonyl-7)- and β-[2-methyl-3-(3,4-trimethylenedioxy) phenylchromonyl-7]glycosides of the methyl ester of N-acetylmuramoyl-L-alanyl-D-isoglutamine, new derivatives of a muramoyldipeptide with chromone aglycones, is described. The starting arylglycosides of N-acetylglucosamine are prepared by glycosylation of 7-hydroxychromone derivatives with the peracetate of α-glucosamine chloride catalyzed by a crown ether. The synthesized β-aryl-4,6-O-isopropylidene-N-acetylmuramic acids are condensed with the dipeptide and deprotected to give the desired glycopeptides.