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Synthesis and characterization by 1H and 13C nuclear magnetic resonance spectroscopy of 17α-hexanoic derivatives of 5α-dihydrotestosterone and testosterone
| Content Provider | Semantic Scholar |
|---|---|
| Author | Mappus, Elisabeth Renaud, Mélanie Ravel, Marc Rolland De Grenot, Catherine Cuilleron, Claude Y. |
| Copyright Year | 1992 |
| Abstract | Abstract The synthesis and characterisation of 17α-(6'-hexanoic acid) derivatives of 5α-dihydrotestosterone and testosterone, useful as ligands for affinity chromatography purification or as precursors for affinitylabeling of androgen-binding proteins, is described. Alkynylation of 3-ethylenedioxy-, 3β-hydroxy-, and 3β,5-dihydroxy-5α-androstan-17-one precursors with the potassium derivative of 5-hexyn-1-ol led to the corresponding 17α-(6'-hydroxyhex-1'-ynyl) derivatives, which were hydrogenated over 10% Pt-C catalyst to give 17α-(6'-hydroxyhexyl) derivatives. Chromic acid oxidation of the primary hydroxy group of the 3-ethylenedioxy-17-hexyl intermediate into carboxylic acid followed by acid cleavage of the 3-ketal group gave 17α-(5'-carboxypentyl)-5α-dihydrotestosterone, which was also obtained directly by chromic acid oxidation of the 3β-hydroxy intermediate. Chromic acid oxidation of the primary hydroxy group of the 3β,5α-dihydroxy precursor resulted in a 5α-hydroxy-3-oxo intermediate, which was dehydrated to give 17α-(5'-carboxypentyl)testosterone. The 17α configuration of these derivatives and of synthetic precursors was established by comparing their molecular rotations and their 1 H and 13 C nuclear magnetic resonance (NMR) spectra including solvent effects, with data reported for 17α- or 17β-substituted steroid analogs as well as with 1 H and 13 C NMR reference data recorded in this work for 17α-ethynyltesfosterone, 17α-ethynyl-19-nortestosterone, 17α-ethyl-19-nortestosterone, 17αmethyltestosterone, and 17α-methyl-5α-dihydrotestosterone. |
| Starting Page | 122 |
| Ending Page | 134 |
| Page Count | 13 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/0039-128X(92)90070-P |
| Volume Number | 57 |
| Alternate Webpage(s) | https://api.elsevier.com/content/article/pii/0039128X9290070P |
| Alternate Webpage(s) | https://www.sciencedirect.com/science/article/pii/0039128X9290070P?dgcid=api_sd_search-api-endpoint |
| Alternate Webpage(s) | https://doi.org/10.1016/0039-128X%2892%2990070-P |
| Journal | Steroids |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
