Tiomesterone
From Wikipedia, the free encyclopedia
| Tiomesterone | ||
|---|---|---|
 | ||
| IUPAC name S-[(1S,7R,8S,9S,10R,13S,14S,17S)-1-acetylsulfanyl-17-hydroxy-10,13,17-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-7-yl] ethanethioate | ||
| Other names Thiomesterone; Thiomestrone | ||
| Identifiers | ||
| CAS number | 2205-73-4  | |
| PubChem | 16626 | |
| Jmol-3D images | {{#if:CC(=O)S[C@@H]1CC2=CC(=O)C[C@@H]([C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C)O)C)SC(=O)C|Image 1 | |
| ||
| Properties | ||
| Molecular formula | C24H34O4S2 | |
| Molar mass | 450.65 g/mol | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Tiomesterone is an anabolic steroid.
Synthesis
Extension of the chain of double bonds in androstenes provides yet another site for modifying the basic structure.
Bromination of the intermediate () that features the 1,4-dien-3-one system proceed on the allylic position at C6 (). Dehydrobromination by means of lithium carbonate in DMF leads to formation of the 1,4,6-trien-3-one system (). Treatment of that intermediate with thioacetic acid proceeds to add one thiol group to each end of the conjugated systems to afford the bisthiolated product thiomestrone ().
| ||||||||||||||||||||||||||||||||||||||
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.