23893-13-2Relevant academic research and scientific papers
The Chemistry od Erythromycin. Reactions of Erythromycin A Imine and its 6-Methyl Ether with Aldehydes and Hydrazines
Davies, J. Sydney,Hunt, Eric,Zomaya, Iskander I.
, p. 1409 - 1414 (2007/10/02)
Erythromycin imine (3) and its 6-methyl ether (6) are multifunctional N-unsubstituted imines, which, in contrast to most unsubstituted imines, are readily isolable and relatively stable towards hydrolysis.With aldehydes in ethanol, the imines react quite differently: the imine (3) reacts with aliphatic and aromatic aldehydes to give predominantly the 9,11-cyclic imines (9), whereas the ether (6) reacts with aliphatic aldehydes to give N-(1-ethoxyalkyl)imines (13) and with benzaldehyde to give a 9,12-epoxy Schiff's base derivative (12).The imines also differ in their reactivities towards hydrazine derivatives: the imine (3) readily reacts with monosubstituted hydrazines to form erythromycin hydrazone derivatives, whereas the ether (6), in common with erythromycin (1), is unreactive towards these reagents.A rationale for the different modes of reaction of compounds (3) and (6) is discussed.
Translactonization in Erythromycins
Kibwage, Isaac O.,Busson, Roger,Janssen, Gerard,Hoogmartens, Jos,Vanderhaeghe, Hubert
, p. 990 - 996 (2007/10/02)
When erythromycin A is heated in diethylamine-acetic acid, an erythromycin hemiketal is obtained, which can be further transformed into a new enol ether and spiroketal.The new enol ether is also obtained in equilibrium with the normal one on heating erythromycin A or B in pyridine-acetic acid.The novel compounds, which will be called pseudoerythromycin derivatives, are characterized by a translactonization between the C11-hydroxyl and the lactone group.Their structure was proved by mass and 1H and 13C NMR spectrometry, by acetylation experiments, and by degradation with lead tetraacetate.
