3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-acetate

Base Information

• Chemical Name: 3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-acetate
• CAS No.: 1474-10-8
• Molecular Formula: C23H34 O5
• Molecular Weight: 390.52
• European Community (EC) Number: 216-015-2
• DSSTox Substance ID: DTXSID30933115
• Nikkaji Number: J22.719F
• Wikidata: Q82908916
• Mol file: 1474-10-8.mol

Synonyms:1474-10-8;3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-acetate;EINECS 216-015-2;[2-[(3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;3,17-dihydroxy-20-oxopregn-5-en-21-yl acetate;SCHEMBL10949227;DTXSID30933115;21-Acetoxy-3beta,17alpha-dihydroxypregn-5-en-20-one;Pregn-5-en-20-one, 21-(acetyloxy)-3,17-dihydroxy-, (3.beta.)-

Chemical Property of 3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-acetate

Chemical Property:

• Vapor Pressure: 1.32E-13mmHg at 25°C
• Boiling Point: 533.4°C at 760 mmHg
• Flash Point: 179.1°C
• PSA: 83.83000
• Density: 1.21g/cm³
• LogP: 3.17340
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 714

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)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O

Technology Process of 3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-acetate

There total 13 articles about 3-beta,17-alpha,21-Trihydroxypregn-5-en-20-one 21-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:

17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one (3517-42-8) → 3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate (1474-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol. sodium methylate

2: pyridine

With pyridine; sodium methylate;

DOI:10.1021/jo01373a017

Reference yield:

3β,17α,21-trihydroxypregn-5-en-20-one 3-tetrahydropyranyl 21-acetate (88261-16-9) → 3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate (1474-10-8)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 50 ℃; for 0.333333h;

Reference yield:

methyl 20-cyano-3β-hydroxypregna-5,17(20)-dien-21-oate (88261-10-3) → 3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate (1474-10-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / p-TsOH / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 67 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: 83 percent / pyridine / Ambient temperature

4: 47 percent / KMnO₄, triethylbenzylammonium chloride (TEBACl) / CH₂Cl₂ / Ambient temperature

5: p-TsOH, methanol / 0.33 h / 50 °C

With pyridine; methanol; potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In hexane; dichloromethane;

upstream raw materials:

17-Hydroxypregnenolone

21-acetoxy-5,6β-dichloro-3β,17-dihydroxy-5α-pregnan-20-one

3β,17α,21-trihydroxypregn-5-en-20-one

acetic anhydride

Downstream raw materials:

6β,17α,21-trihydroxypregn-4-ene-3,20-dione

cortexolone 21-acetate

3β,17,21-triacetoxy-pregn-5-en-20-one

17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one

Refernces

• 1、 Cutler et al.. "-". . p. 1629,1632. Retrieved 1959.