Synthesis of a phenyl beta-avobioside derivative of the disaccharide component of avoparcins.
The synthesis of the phenyl beta-glycoside of avobiose, a disaccharide fragment present in the antibiotic avoparcin, is reported. It is based on glycosylation of phenyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside with 2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-ribo-hex- 1-enitol, a fully protected glycal of L-ristosamine, in the presence of trimethylsilyl triflate.
Dong
X
X
Laboratoire de Chimie, Section Biologie, Institut Curie, Paris, France.
Tillequin
F
F
Monneret
C
C
Horvath
G
G
Sztaricskai
F
F
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides
D000900:Anti-Bacterial Agents; D004187:Disaccharides; D006020:Glycopeptides; C016249:avoparcin