20976-92-5

Usage

Type

Synthetic steroid hormone

Class

Pregane steroids

Derivative of

Progesterone

Usage

Development of pharmaceutical drugs (hormone replacement therapy, contraceptive pills)

Molecular structure

Pregnane core with a methyl group at the 20th carbon and hydroxyl groups at the 3rd and 20th carbon positions

Activity

Potent hormonal activity

Function

Regulating physiological processes in the body

Importance

Compound in pharmacology and medicine

InChI:InChI=1/C22H36O2/c1-20(2,24)19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,3)18(16)10-12-22(17,19)4/h5,15-19,23-24H,6-13H2,1-4H3/t15-,16-,17-,18-,19+,21-,22-/m0/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 20917-51-5 20-hydroxy-20-methylpregn-4-en-3-one 
• 53-43-0 dehydroepiandrosterone 
• 853-23-6 prasterone acetate 
• 983-28-8 3β-acetoxy-17-(2-carbamoylhydrazono)-5-androstene 

Relevant academic research and scientific papers

The biosynthesis of 34,24 dinor 5 cholene 3β,20 diol and 23,24 dinor 5 cholene 3β,21 diol

An alternative pathway for steroidogenesis, via a sesterterpene, was proposed. This communication presents evidence that 2 of the proposed compounds with the 23,24 dinorcholane carbocyclic system, 23,24 dinor 5 cholene 3β,20 diol and 23,24 dinor 5 cholene 3β,21 diol, can be biosynthesized from sodium [3H] acetate in a bovine adrenal preparation.

An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans

The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.