3-beta,21-Dihydroxypregn-5-en-20-one di(acetate)

Base Information

• Chemical Name: 3-beta,21-Dihydroxypregn-5-en-20-one di(acetate)
• CAS No.: 1693-63-6
• Molecular Formula: C25H36 O5
• Molecular Weight: 416.558
• European Community (EC) Number: 216-896-3
• Nikkaji Number: J195.341I
• Mol file: 1693-63-6.mol

Synonyms:3 beta,21-diacetoxy-5-pregnen-20-one;3,21-DAXPG-20

Chemical Property of 3-beta,21-Dihydroxypregn-5-en-20-one di(acetate)

Chemical Property:

• Vapor Pressure: 1.93E-10mmHg at 25°C
• Melting Point: 165.5-167 °C
• Boiling Point: 508°Cat760mmHg
• Flash Point: 216.7°C
• PSA: 69.67000
• Density: 1.14g/cm³
• LogP: 4.62930
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 416.25627424
• Heavy Atom Count: 30
• Complexity: 770

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: CC(=O)OCC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
• Uses: NSC 226895 is an intermediate in the synthesis of Sodium 3-hydroxy-androst-5-ene-17-methylsulfate (S333300), a derivative of the pheromone Androstenone. Androstenone (CAS# 18339-16-7) is a potent androgen with anabolic properties.

Technology Process of 3-beta,21-Dihydroxypregn-5-en-20-one di(acetate)

There total 35 articles about 3-beta,21-Dihydroxypregn-5-en-20-one di(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: 99.0%

21-hydroxypregnenolone (1164-98-3) → 3β,21-diacetoxypregn-5-en-20-one (1693-63-6)

Guidance literature:

With acetic anhydride; toluene-4-sulfonic acid; In ice-water; acetic acid;

Reference yield: 95.0%

21-hydroxypregnenolone (1164-98-3) + acetic anhydride (108-24-7) → 3β,21-diacetoxypregn-5-en-20-one (1693-63-6)

Guidance literature:

With pyridine;

DOI:10.1021/jo00136a035

Reference yield: 95.0%

21-acetoxypregnenolone (566-78-9) + acetic anhydride (108-24-7) → 3β,21-diacetoxypregn-5-en-20-one (1693-63-6)

Guidance literature:

With p-toluenesulfonic acid monohydrate; for 0.166667h; Microwave irradiation;

DOI:10.1016/j.steroids.2009.12.004

upstream raw materials:

21-bromo-3β-hydroxy-5-pregnen-20-one 3-acetate

sodium acetate

Pregnenolone acetate

acetic anhydride

Downstream raw materials:

21-hydroxypregnenolone

(5'R)-3β-acetoxy-17β-[2-(2-chlorophenyl)-phenyl-4,5-dihydrooxazol-5-yl]androst-5-ene

(5'R)-3β-acetoxy-17β-[2-(4-fluorophenyl)-phenyl-4,5-dihydrooxazol-5-yl]androst-5-ene

(5'R)-3β-acetoxy-17β-[2-(4-bromophenyl)-phenyl-4,5-dihydrooxazol-5-yl]androst-5-ene

Refernces

• 1、 Barton, Derek H. R.,Motherwell, William B.,Zard, Samir Z.. "A Simple Construction of the Hydroxy-ketone Side Chain of Corticosteroids from 17-Oxo-steroids via Nitro-olefins". . p. 551 - 552. Retrieved 1982.
• 2、 Moffett,Weisblat. "-". . p. 2183. Retrieved 1952.
• 3、 Banday, Abid H.,Giri, Aswini K.,Parveen, Rifat,Bashir, Nusrat. "Design and synthesis of D-ring steroidal isoxazolines and oxazolines as potential antiproliferative agents against LNCaP, PC-3 and DU-145 cells (Dedicated to Prof. Mushtaq A. Qureishi for his pioneering contribution to Natural Product Research at University of Kashmir)". . p. 93 - 98. Retrieved 2014/07/08.
• 4、 Kim, Tae-Kang,Chen, Jianjun,Li, Wei,Zjawiony, Jordan,Miller, Duane,Janjetovic, Zorica,Tuckey, Robert C.,Slominski, Andrzej. "A new steroidal 5,7-diene derivative, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid, shows potent anti-proliferative activity". experimental part. p. 230 - 239. Retrieved 2010/04/29.