3,17-Diacetyloxypregna-3,5-dien-20-one

Base Information

• Chemical Name: 3,17-Diacetyloxypregna-3,5-dien-20-one
• CAS No.: 4954-07-8
• Molecular Formula: C25H34 O5
• Molecular Weight: 414.542
• Mol file: 4954-07-8.mol

Synonyms:Pregna-3,5-dien-20-one,3,17-dihydroxy-, diacetate (6CI,7CI,8CI)

Chemical Property of 3,17-Diacetyloxypregna-3,5-dien-20-one

Chemical Property:

• Melting Point: 196 - 204 °C
• PSA: 69.67000
• LogP: 4.89700
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

3,17-Dihydroxy-pregna-3,5-dien-20-one Diacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A steroid used in the preparation of Cyproterone acetate (C989100) impurities. 3,17-Dihydroxy-pregna-3,5-dien-20-one Diacetate is a steroid used in the preparation of Cyproterone acetate.

Technology Process of 3,17-Diacetyloxypregna-3,5-dien-20-one

There total 7 articles about 3,17-Diacetyloxypregna-3,5-dien-20-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: 92.0%

17-hydroxyprogesterone (68-96-2) + acetic anhydride (108-24-7) → pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate (4954-07-8)

Guidance literature:

With perchloric acid; In ethyl acetate; for 0.1h;

DOI:10.1016/0039-128X(95)00170-U

Reference yield:

17-hydroxyprogesterone (68-96-2) + acetic anhydride (108-24-7) → hydroxyprogesterone acetate (4134-58-1,17308-02-0,41460-93-9,41460-97-3,630-56-8,302-23-8) + pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate (4954-07-8) + Acetic acid (8R,9S,10R,13S,14S,17R)-3-acetoxy-17-(1-acetoxy-vinyl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Guidance literature:

With toluene-4-sulfonic acid; for 0.0833333h; microwave irradiation;

DOI:10.1016/S0040-4020(03)00207-2

Reference yield:

3,5-pregnadien-3,17-diol-20-one-3-methyl ether (1048-89-1) → pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate (4954-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

2: perchloric acid / ethyl acetate / 0.5 h / 20 °C

With perchloric acid; trifluoroacetic acid; In dichloromethane; ethyl acetate;

DOI:10.1002/jlcr.3114

upstream raw materials:

hydroxyprogesterone acetate

acetic anhydride

acetyl chloride

17-hydroxyprogesterone

Downstream raw materials:

17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione

17-Hydroxypregnenolone

pregn-5-ene-3β,17α-diol-20-one 17-acetate

hydroxyprogesterone acetate

Refernces

• 1、 -. "Preparation method of 6-methylene-17alpha-hydroxyprogesterone acetate". Paragraph 0026-0027; 0030-0031; 0034-0035; 0038-0039. . Retrieved 2017/08/29.
• 2、 Joannou,Reeder. "15β-Hydroxysteroids (part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20- one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione". . p. 18 - 21. Retrieved 2007/10/03.