Tiomesterone

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Tiomesterone
Tiomesterone structure.svg
Identifiers
CAS number 2205-73-4 YesY
PubChem 16626
Jmol-3D images Image 1
Properties
Molecular formula C24H34O4S2
Molar mass 450.65 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Tiomesterone is an anabolic steroid.

Synthesis[edit]

Extension of the chain of double bonds in androstenes provides yet another site for modifying the basic structure.

Thiomestrone synthesis.png

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.[1]

References[edit]

  1. ^ Krämer, J. M.; Brückner, K.; Irmscher, K.; Bork, K. H. (1963). "Darstellung von mercapto-substituierten 3-Keto-steroiden der Androstan-Reihe". Chemische Berichte 96 (10): 2803. doi:10.1002/cber.19630961040.  edit