Epimerization of erythromycin derivatives.
Dirithromycin (3) isomerizes upon dissolution in different solvents. From X-ray analysis of V-T 108, an analogue of dirithromycin, and comparative 1H and 13C NMR, and MS data, the isomer of dirithromycin was confirmed to be the C-16-(S)-epimer. The ratio of the two epimers at equilibrium conditions was approximately 8:2 (R/S) in methanol at room temperature.
Firl
J
J
Organisch-chemisches Institut, Technische Universität München, Garching, FRG.
Prox
A
A
Luger
P
P
Maier
R
R
Woitun
E
E
Daneck
K
K
D000900:Anti-Bacterial Agents; D002855:Chromatography, Thin Layer; D003460:Crystallization; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000737:chemistry; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D018942:Macrolides; C053853:dirithromycin; D004917:Erythromycin