Tiomesterone

Tiomesterone
Names
	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 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.016.923
PubChem CID	16626;
CompTox Dashboard (EPA)	DTXSID50176527 ;
	SMILES 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;
Properties
Chemical formula	C24H34O4S2
Molar mass	450.65 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 ().

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