16375-99-8Relevant academic research and scientific papers
15β-hydroxysteroids (Part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers
Reeder, Anthony Y.,Joannou, George E.
, p. 221 - 225 (2007/10/03)
We report the synthesis of 10 novel steroids obtained from 3β,15β- diacetoxy-17α-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15β-acetoxy-20-20-ethylenedioxy-17α-hydroxy- 1,2,6,7-3-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3β,15β,17α-trihydroxy-5-pregnen-20-one (1a) and 3α,15β,17α- trihydroxy-5β-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3β,15β,17α- trihydroxy-1,2,7-3H-pregn-5-en-20-one (1d) and 3α,15β,17α-trihydroxy- 1,2,6,7-3H-5β-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15β,17α-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15β-hydroxysteroid metabolites.
15β-Hydroxysteroids (part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20- one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione
Joannou,Reeder
, p. 18 - 21 (2007/10/03)
A simple three-step synthetic method is reported on the conversion of Δ4-3-ketosteroids to the corresponding 3β- hydroxy-Δ5-steroid analogues. 17α-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3β,17α-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17α-diacetoxy-3,5-pregnadien-20-one (14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15β,17α-dihydroxy-4-pregnen- 3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3β, 15β, 17α-trihydroxy-5-pregnen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3,15β,17α-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydrice gave 5-pregnen-3β,15β,17α, 20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with metanolic sodium hydroxide the desired product 3β,15β,17α-trihydroxy-5-pregnen-20-one (1) in good yield (54%).
