Androst-2-ene-3,17-diyl diacetate

Base Information

• Chemical Name: Androst-2-ene-3,17-diyl diacetate
• CAS No.: 981-64-6
• Molecular Formula: C23H34O4
• Molecular Weight: 374.521
• NSC Number: 119006
• DSSTox Substance ID: DTXSID70913451
• Mol file: 981-64-6.mol

Synonyms:981-64-6;androst-2-ene-3,17-diyl diacetate;NSC119006;DTXSID70913451;NSC-119006

Chemical Property of Androst-2-ene-3,17-diyl diacetate

Chemical Property:

• Vapor Pressure: 9.43E-09mmHg at 25°C
• Boiling Point: 463°Cat760mmHg
• Flash Point: 223.8°C
• Density: 1.12g/cm³
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 374.24570956
• Heavy Atom Count: 27
• Complexity: 667

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2C1(CCC3C2CCC4C3(CC=C(C4)OC(=O)C)C)C

Technology Process of Androst-2-ene-3,17-diyl diacetate

There total 18 articles about Androst-2-ene-3,17-diyl diacetate 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: 78.0%

Stanolone (521-18-6) + acetic anhydride (108-24-7) → (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate (981-64-6)

Guidance literature:

With perchloric acid; In ethyl acetate;

DOI:10.1021/jo00050a002

Reference yield: 74.0%

acetic anhydride (108-24-7) + 17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one (58701-44-3) → (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate (981-64-6)

Guidance literature:

With perchloric acid; In ethyl acetate; Ambient temperature;

DOI:10.1021/jo00101a052

Reference yield:

3,17-diacetoxy-5α-androsta-2,16-diene (28312-74-5) → (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate (981-64-6)

Guidance literature:

With 1,4-dioxane; Lindlar's catalyst; Hydrogenation;

upstream raw materials:

stanolone acetate

3,17-diacetoxy-5α-androsta-2,16-diene

acetyl chloride

Stanolone

Downstream raw materials:

5α-androstan-2α-fluoro-3-one-17β-ol acetate

5alpha-Androstane-2beta-fluoro-17beta-ol-3-one acetate

Acetic acid (5S,8R,9S,10S,13S,14S,17S)-17-acetoxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester

17β-acetoxy-2α-bromo-5α-androstan-3-one

Refernces

• 1、 He, Rong-De,Li, Chun-Ling,Pan, Qiu-Quan,Guo, Peng,Liu, Xue-Yuan,Shu, Xing-Zhong. "Reductive Coupling between C-N and C-O Electrophiles". supporting information. p. 12481 - 12486. Retrieved 2019/09/04.
• 2、 Heathcock,Smith. "Synthesis and biological activity of unsymmetrical bis-steroidal pyrazines related to the cytotoxic marine natural product cephalostatin 1". . p. 6828 - 6839. Retrieved 2007/10/02.