| Identification | Back Directory | [Name]
5.alpha.-Androstan-3-one, 17.beta.-hydroxy-2-(hydroxymethylene)- | [CAS]
4033-95-8 | [Synonyms]
4,5α-Dihydro-2-(hydroxymethylene)testosterone
4,5alpha-Dihydro-2-(hydroxymethylene)testosterone
5.alpha.-Androstan-3-one, 17.beta.-hydroxy-2-(hydroxymethylene)- | [Molecular Formula]
C20H30O3 | [MOL File]
4033-95-8.mol | [Molecular Weight]
318.45 |
| Hazard Information | Back Directory | [Definition]
ChEBI: 4,5alpha-Dihydro-2-(hydroxymethylene)testosterone is a 3-oxo-5alpha-steroid. | [Synthesis]
4,5α-dihydro-2-(hydroxymethylene)testosterone (oxystanolone) is obtained by reacting 2-Hydroxymethylene-androstan-17β-((tetrahydro-2H-pyran-2-yl)oxy)-3-one with pyridinium tosylate.
Procedure: To a solution of 0.95 g intermediate (2) in 55 ml of the solvent mixture
tetrahydrofuran/methanol/water 7:2:1 pyridinium tosylate (1.15 g dissolved in 20 ml
tetrahydrofuran/methanol/water 7:2:1) was added at room temperature. Subsequently, this was
followed by 8 h stirring at 50°C. Monitoring via TLC still shows remaining starting material.
After evaporation of all solvents, the crude product was chromatographed on silica gel by using
hexane-ethyl acetate (8:2). 0.385 g of 5 was obtained as a colorless solid (52%). |
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