Issue 10, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Ketone–hemiacetal tautomerism in erythromycin A in non-aqueous solutions. An NMR spectroscopic study

Jeremy R. Everett,   Eric Hunt  and  John W. Tyler  

Abstract

NMR spectroscopic studies, including 13C SIMPLE NMR, in a number of solvents, show that erythromycin A exists as a mixture of the 9-ketone (the predominant species), one 6,9-cyclic hemiacetal 3(9-deoxo-6-deoxy-9-hydroxy-6,9-epoxyerythromycin A), and one 9,12-cyclic hemiacetal 2(9-deoxo-12-deoxy-9-hydroxy-9,12-epoxyerythromycin A). Similar studies on the 4″,11-diacetate of erythromycin A, previously thought to be the 6,9-cyclic hemiacetal, show that this exists exclusively as the 9,12-cyclic hemiacetal 4(9-deoxo-12-deoxy-9-hydroxy-9,12-epoxyerythromycin A 4″,11-diacetate) in CDCl3. The (9S) stereochemistry is proposed for 2, 3 and 4. The factors governing tautomerism in erythromycin A and its derivative are discussed.

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Article information

DOI
https://doi.org/10.1039/P29910001481
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 1481-1487

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Ketone–hemiacetal tautomerism in erythromycin A in non-aqueous solutions. An NMR spectroscopic study

J. R. Everett, E. Hunt and J. W. Tyler, J. Chem. Soc., Perkin Trans. 2, 1991, 1481 DOI: 10.1039/P29910001481

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