(3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

Base Information

• Chemical Name: (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one
• CAS No.: 58507-05-4
• Molecular Formula: C₁₉H₂₉BrO
• Molecular Weight: 353.343
• Mol file: 58507-05-4.mol

Synonyms:(3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

Chemical Property of (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one

There total 1 articles about (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

3β-tosyloxy-5α-androstan-17-one (10429-07-9) → 5α-androst-2-en-17-one (14639-79-3,24174-20-7,82467-84-3,963-75-7) + (3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one (58507-05-4) + (3R,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one (53512-66-6)

Guidance literature:

With lithium bromide; In acetone; for 72h; Heating;

DOI:10.1021/ja00310a046

Reference yield: 95.0%

(3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one (58507-05-4) → 5alpha-androstan-17-one (963-74-6)

Guidance literature:

With water; zinc; In acetonitrile; at 80 ℃; for 36h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.9b02026

Reference yield: 41.0%

(3S,5S,8R,9S,10S,13S,14S)-3-bromo-10,13-dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one (58507-05-4) + 1-phenyl-propan-1-one (93-55-0) → (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-3-(3-oxo-3-phenylpropyl)hexadecahydro-17H-cyclopenta[a]phenan-t hren-17-one

Guidance literature:

With tris(isopropyl)phosphonium tetrafluoroborate; palladium diacetate; copper(II) dipivaloate; caesium carbonate; acetic acid; In acetic acid methyl ester; benzene; at 90 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.8b03530

upstream raw materials:

3β-tosyloxy-5α-androstan-17-one

Downstream raw materials:

5alpha-androstan-17-one