Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones
20‐Methylpregna‐4,20‐dien‐3‐one and the corresponding 17α‐hydroxy, 20‐hydroxymethyl and 17α‐hydroxy‐20‐hydroxymethyl derivatives were prepared from the 20‐keto compounds by Wittig reaction or a modified Simmons‐Smith reaction. The 13C NMR spectra of these steroids and of 3‐methylene derivatives are...
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todo:paper_07491581_v26_n11_p963_Gonzalez2023-10-03T15:39:17Z Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones Gonzalez, M.D. Burton, G. 13C NMR Steroid hormones 20‐Methylenepregnanes 3‐Methylenepregnanes Synthesis 20‐Methylpregna‐4,20‐dien‐3‐one and the corresponding 17α‐hydroxy, 20‐hydroxymethyl and 17α‐hydroxy‐20‐hydroxymethyl derivatives were prepared from the 20‐keto compounds by Wittig reaction or a modified Simmons‐Smith reaction. The 13C NMR spectra of these steroids and of 3‐methylene derivatives are analysed. Solvent effects produced by addition of methanol‐d4 in the spectra of the 20‐methylene steroids are correlated with intramolecular hydrogen bonding in the corresponding 20‐ketosteroids. Copyright © 1988 John Wiley & Sons, Ltd. Fil:Gonzalez, M.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_07491581_v26_n11_p963_Gonzalez |
| institution |
Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
13C NMR Steroid hormones 20‐Methylenepregnanes 3‐Methylenepregnanes Synthesis |
| spellingShingle |
13C NMR Steroid hormones 20‐Methylenepregnanes 3‐Methylenepregnanes Synthesis Gonzalez, M.D. Burton, G. Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| topic_facet |
13C NMR Steroid hormones 20‐Methylenepregnanes 3‐Methylenepregnanes Synthesis |
| description |
20‐Methylpregna‐4,20‐dien‐3‐one and the corresponding 17α‐hydroxy, 20‐hydroxymethyl and 17α‐hydroxy‐20‐hydroxymethyl derivatives were prepared from the 20‐keto compounds by Wittig reaction or a modified Simmons‐Smith reaction. The 13C NMR spectra of these steroids and of 3‐methylene derivatives are analysed. Solvent effects produced by addition of methanol‐d4 in the spectra of the 20‐methylene steroids are correlated with intramolecular hydrogen bonding in the corresponding 20‐ketosteroids. Copyright © 1988 John Wiley & Sons, Ltd. |
| format |
JOUR |
| author |
Gonzalez, M.D. Burton, G. |
| author_facet |
Gonzalez, M.D. Burton, G. |
| author_sort |
Gonzalez, M.D. |
| title |
Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| title_short |
Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| title_full |
Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| title_fullStr |
Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| title_full_unstemmed |
Preparation and carbon‐13 NMR study of 3‐ and 20‐methylene analogues of steroid hormones |
| title_sort |
preparation and carbon‐13 nmr study of 3‐ and 20‐methylene analogues of steroid hormones |
| url |
http://hdl.handle.net/20.500.12110/paper_07491581_v26_n11_p963_Gonzalez |
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AT gonzalezmd preparationandcarbon13nmrstudyof3and20methyleneanaloguesofsteroidhormones AT burtong preparationandcarbon13nmrstudyof3and20methyleneanaloguesofsteroidhormones |
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