Androsta-5,16-dien-3-yl acetate

Base Information

• Chemical Name: Androsta-5,16-dien-3-yl acetate
• CAS No.: 1236-14-2
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.468
• NSC Number: 131018
• DSSTox Substance ID: DTXSID90924549
• Mol file: 1236-14-2.mol

Synonyms:androsta-5,16-dien-3-yl acetate;1236-14-2;NSC131018;DTXSID90924549;AKOS024341941;NSC-131018

Chemical Property of Androsta-5,16-dien-3-yl acetate

Chemical Property:

• Vapor Pressure: 1.51E-06mmHg at 25°C
• Boiling Point: 398.1°C at 760 mmHg
• Flash Point: 189.2°C
• Density: 1.07g/cm³
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 574

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C=CCC4C3CC=C2C1)C)C

Technology Process of Androsta-5,16-dien-3-yl acetate

There total 3 articles about Androsta-5,16-dien-3-yl acetate 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: 80.0%

Tributyl-[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-stannane (136321-38-5) + acetyl chloride (75-36-5) → 3β-acetoxyandrost-5,16-diene (1236-14-2) + 16-dehydropregnenolone acetate (979-02-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(benzonitrile)palladium(II) dichloride; at 80 ℃; for 8h;

DOI:10.1002/prac.19933350508

Reference yield: 60.0%

acetyl chloride (75-36-5) + Acetic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-tributylstannanyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester → 3β-acetoxyandrost-5,16-diene (1236-14-2) + 16-dehydropregnenolone acetate (979-02-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(benzonitrile)palladium(II) dichloride; at 80 ℃; for 8h;

DOI:10.1002/prac.19933350508

Reference yield: 17.0%

5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate (1259-22-9) → prasterone acetate (853-23-6) + 3β-acetoxyandrost-5,16-diene (1236-14-2) + 17α-hydroxyandrost-5-en-3β-yl 3-acetate (100428-85-1)

Guidance literature:

With sodium nitrite; In dimethyl sulfoxide; at 135 ℃; for 1h;

DOI:10.1135/cccc19930600

upstream raw materials:

5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate

Tributyl-[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-stannane

acetyl chloride

Downstream raw materials:

abiraterone acetate

Refernces

• 1、 Schweder, Bernd,Uhlig, Egon,Doering, Manfred,Kosemund, Dirk. "Δ16-20-Ketosteroids by C2-Elongation from Δ16-17-Substituted Steroids". . p. 439 - 444. Retrieved 2007/10/02.