This paper demonstrates that the crystallization of 3b-acetoxy-14a,15a-epoxy-5a-cholest-8-en-7-one from methanol affords the 3b-acetoxy-9a-methoxy-15a-hydroxycholest-8(14)-en-7-one. The structure of this steroid, which shows an apparently anomalous UV absorption maximum, is determined by high field NMR experiments, supporting the coupling constant values assignments and the NOE contacts by a conformational study through theoretical calculations at the B3LYP/6-31G* level. The computational study also justifies the observed UV absorption of the steroid, thus demonstrating the usefulness of computer chemistry in providing support for the identification of unknown compounds.

Elucidation of the opening of the epoxidic ring of the 3beta-acetoxy-14alpha,15alpha-epoxy-5alpha-cholest-8-en-7-one by methanol, using NMR techniques assisted by a conformational study through theoretical calculations / M. Anastasia, P. Allevi, R. Colombo, E. Giannini. - In: STEROIDS. - ISSN 0039-128X. - 72:11-12(2007 Oct), pp. 809-818.

Elucidation of the opening of the epoxidic ring of the 3beta-acetoxy-14alpha,15alpha-epoxy-5alpha-cholest-8-en-7-one by methanol, using NMR techniques assisted by a conformational study through theoretical calculations

M. Anastasia
Primo
;
P. Allevi
Secondo
;
R. Colombo
Penultimo
;
E. Giannini
Ultimo
2007-10

Abstract

This paper demonstrates that the crystallization of 3b-acetoxy-14a,15a-epoxy-5a-cholest-8-en-7-one from methanol affords the 3b-acetoxy-9a-methoxy-15a-hydroxycholest-8(14)-en-7-one. The structure of this steroid, which shows an apparently anomalous UV absorption maximum, is determined by high field NMR experiments, supporting the coupling constant values assignments and the NOE contacts by a conformational study through theoretical calculations at the B3LYP/6-31G* level. The computational study also justifies the observed UV absorption of the steroid, thus demonstrating the usefulness of computer chemistry in providing support for the identification of unknown compounds.
Oxidation ; 3-Chloroperoxybenzoic acid ; 3b-Acetoxy-5a-cholesta-8,14-dien- 7-one Epoxide
Settore BIO/10 - Biochimica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/33631
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