Steroide—XLIV : 1H-NMR-untersuchungen. Konfigurationszuordnung 16,17-disubstituierter steroide |
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| Authors: | Von B Schönecker D Tresselt K Ponsold |
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| Institution: | 1. Akademie der Wissenschaften der DDR, Forschungszentrum für Molekularbiologie und Medizin, Zentralinstitut für Mikrobiologie und experimentelle Therapie, DDR-69 Jena, Abteilung Steroidsynthese Germany;2. Akademie der Wissenschaften der DDR, Forschungszentrum für Molekularbiologie und Medizin, Zentralinstitut für Mikrobiologie und experimentelle Therapie, DDR-69 Jena, Abteilung Biophysikochemie Germany |
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| Abstract: | 1H-NMR-spectra of 16,17-disubstituted estra-1,3,5(10)-trienes and androstanes are discussed with regard to the determination of the configuration in the positions 16 and 17. The availability of the coupling constant J16,17, the chemical shift of the 13β-methyl protons, the chemical shift of the 17-proton and both the chemical shift and the sum of the coupling constants of the 16-proton is investigated for the elucidation of unknown configurations at C-16 and C-17. 16β,17α-Configuration of the substituents was found to be distinguished from the other three configurations by a low coupling constant J16,17 (≦2 Hz). For the determination of the other configurations the coupling constant J16,17 was also used together with the other data. Esterification of the 17-hydroxy group or its reaction with trichloracetylisocyanate caused a low field shift of the 17-proton depending on the configuration of the substituents in the positions 16 and 17. This is an additional possibility for the configurational assignment. |
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