A computational approach to the synthesis of dirithromycin

Duran, Dilek and Aviyente, Viktorya and Baysal, Canan (2004) A computational approach to the synthesis of dirithromycin. Journal of molecular modeling, 10 (2). pp. 94-101. ISSN 1610-2940 (Print) 0948-5023 (Online)

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Dirithromycin is a macrolide antibiotic derived from erythromycin A. Dirithromycin is synthesized by the condensation of 9(S)-erythromycylamine with 2-(2-methoxyethoxy)-acetaldehyde. To gain insight into the synthesis, the condensation mechanism has been analyzed computationally by the AM1 method in the gas phase. First, the formation of the Schiff bases of dirithromycin and epidirithromycin from 9(S)-erythromycylamine and 2-(2-methoxyethoxy)-acetaldehyde were modeled. Then, the tautomerization of the Schiff bases to dirithromycin and epidirithromycin were considered. Finally, the epimerization of the Schiff base of epidirithromycin to the Schiff base of dirithromycin was investigated. Our results show that, even though carbinolamine forms faster for epidirithromycin than the corresponding structure for dirithromycin, dirithromycin is the major product of the synthesis.
Item Type: Article
Uncontrolled Keywords: dirithromycin; epidirithromycin; Schiff base; ring-chain tautomerization; epimerization
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Engineering and Natural Sciences
Depositing User: Canan Atılgan
Date Deposited: 16 Feb 2007 02:00
Last Modified: 17 Sep 2019 16:08
URI: https://research.sabanciuniv.edu/id/eprint/313

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