3090-70-8

Basic information

• Product Name: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• Synonyms: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS NO: 3090-70-8
• Molecular Weight: 334.499
• Mol File: 3090-70-8.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(3090-70-8)
• EPA Substance Registry System: (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate(3090-70-8)

Safety Data

• Hazardous Substances Data: 3090-70-8(Hazardous Substances Data)

Usage

General Description

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate is a chemical compound with a complex and lengthy name. It is an acetate derivative of a steroid compound, which means it contains a hydroxyl group and an acetate ester group. The presence of the cyclopenta[a]phenanthren structure indicates that it is a type of steroid hormone. (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate likely has physiological effects on the body due to its steroid nature, potentially influencing processes such as inflammation, immune response, and metabolism. The specific stereochemistry indicated by the (3S,5S,8R,9S,10S,13S,14S,17S) prefix suggests a highly specific three-dimensional arrangement of atoms in the molecule, which can influence its biological activity and function.

Upstream product

• 1639-43-6 androstenediol-3-acetate 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 108-05-4 vinyl acetate 
• 571-20-0 5-androgen-3,17-diol 
• 77-60-1 tigogenin 
• 104597-49-1 3-acetoxy-androst-5-en-17-one 
• 17291-39-3 p-toluenesulfonate of 3β-acetoxy-5α-androstan-17β-ol 
• 95043-80-4 Acetic acid (3S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 95119-02-1 Acetic acid (3R,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 1098-12-0 3β-acetoxy-5α-androstan-17-one 
• 1600-76-6 3β-acetoxy-5α-androstan-17β-ol 
• 111712-88-0 3β-acetoxy-17β-methylsulfonyloxy-5α-androstane 
• 481-29-8 Epiandrosterone 
• 853-23-6 prasterone acetate 

Downstream Products

• 17291-39-3 3β-acetoxy-17β-p-toluenesulfonyloxy-5α-androstan 
• 2722-91-0 17α-amino-5α-androstan-3β-ol 
• 1600-76-6 3β-acetoxy-5α-androstan-17α-ol 
• 61894-45-9 3β-acetoxy-17β-benzoyloxy-5α-androstane 
• 114552-86-2 17β-(toluene-4-sulfonyloxy)-5α-androstan-3β-ol 
• 571-20-0 5-androgen-3,17-diol 
• 17291-39-3 p-toluenesulfonate of 3β-acetoxy-5α-androstan-17β-ol 

Relevant articles and documents

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Silver-mediated oxidative aliphatic C-H trifluoromethylthiolation

The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C-H bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.

Synthesis of 5α-androstan-3β,17β-diol from tigogenin

5α-Androstan-3β,17β-diol (3b-adiol), a known inhibitor of prostate cancer cell growth, was synthesized from tigogenin. Its structure was confirmed by NMR and IR spectroscopy and mass spectroscopy. Springer Science+Business Media, Inc. 2007.