20-Oxopregn-5-ene-3,17-diyl diacetate

Base Information

• Chemical Name: 20-Oxopregn-5-ene-3,17-diyl diacetate
• CAS No.: 3517-38-2
• Molecular Formula: C25H36 O5
• Molecular Weight: 416.558
• European Community (EC) Number: 222-524-0
• NSC Number: 107126,48992,36545
• DSSTox Substance ID: DTXSID80956612
• Mol file: 3517-38-2.mol

Synonyms:17ALPHA-HYDROXYPREGNENOLONE-3,17-DIACETATE;3517-38-2;Pregn-5-en-20-one,17-bis(acetyloxy)-, (3.beta.)-;20-oxopregn-5-ene-3,17-diyl diacetate;NSC48992;DTXSID80956612;NSC36545;NSC-36545;NSC-48992;NSC107126;NSC-107126;FT-0633426

Chemical Property of 20-Oxopregn-5-ene-3,17-diyl diacetate

Chemical Property:

• Boiling Point: 495.6°Cat760mmHg
• Flash Point: 211°C
• PSA: 69.67000
• Density: 1.14g/cm³
• LogP: 4.77180
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 416.25627424
• Heavy Atom Count: 30
• Complexity: 799

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C)OC(=O)C

Technology Process of 20-Oxopregn-5-ene-3,17-diyl diacetate

There total 10 articles about 20-Oxopregn-5-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: 95.0%

pregn-5-ene-3β,17α-diol-20-one 17-acetate (2381-45-5) + acetic anhydride (108-24-7) → 3β,17α-diacetoxypregn-5-en-20-one (3517-38-2)

Guidance literature:

With toluene-4-sulfonic acid; microwave irradiation;

DOI:10.1016/j.steroids.2008.10.017

Reference yield: 90.0%

3β-acetoxy-17α-hydroxy-5-pregnen-20-one (1863-39-4) + acetic anhydride (108-24-7) → 3β,17α-diacetoxypregn-5-en-20-one (3517-38-2)

Guidance literature:

With toluene-4-sulfonic acid; for 0.0333333h; microwave irradiation;

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

Reference yield:

Isopropyl acetate (108-21-4) + 3β-acetoxy-17α-hydroxy-5-pregnen-20-one (1863-39-4) → 3β,17α-diacetoxypregn-5-en-20-one (3517-38-2)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1021/ja01632a032

upstream raw materials:

Isopropyl acetate

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

17-Hydroxypregnenolone

acetic anhydride

Downstream raw materials:

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

3β,17α-Diacetoxypregn-5-en-7,20-dion

Δ⁵-pregnene-3β,17α,20α-triol

Δ⁵-pregnene-3β,17α,20S-triol

Refernces

• 1、 Zmijewski, Michal A.,Li, Wei,Zjawiony, Jordan K.,Sweatman, Trevor W.,Chen, Jianjun,Miller, Duane D.,Slominski, Andrzej T.. "Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β, 17α, 20-triol and their bioactivity in melanoma cells". scheme or table. p. 218 - 228. Retrieved 2009/04/14.
• 2、 Chinn,Desai,Zawadzki. "Possible anchimeric assistance in the hydration decarboxylation of a propiolic acid. Synthesis of methyl 3 (17β acetoxy 3 oxoandrosta 4,6 dien 17α yl)propionate". . p. 1328 - 1331. Retrieved 2007/10/06.