3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-acetate

Base Information

• Chemical Name: 3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-acetate
• CAS No.: 21650-83-9
• Molecular Formula: C23H32 O3
• Molecular Weight: 356.505
• European Community (EC) Number: 244-497-4
• Nikkaji Number: J225.401H
• Mol file: 21650-83-9.mol

Synonyms:3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-acetate;EINECS 244-497-4;NSC 87945;21650-83-9;SCHEMBL9213860;NS00051130

Chemical Property of 3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-acetate

Chemical Property:

• Boiling Point: 468.4°Cat760mmHg
• Flash Point: 202°C
• PSA: 43.37000
• Density: 1.11g/cm³
• LogP: 5.00620
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 356.23514488
• Heavy Atom Count: 26
• Complexity: 702

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(CC=C3C2CCC4C3(CCC(C4)OC(=O)C)C)C
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2[C@@]1(CC=C3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C

Technology Process of 3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-acetate

There total 15 articles about 3beta-Hydroxy-5alpha-pregna-9(11),16-dien-20-one 3-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: 79.0%

C31H46O5 → Acetic acid (3S,5S,10S,13S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (3018-82-4,21650-83-9,108212-03-9)

Guidance literature:

With dihydrogen peroxide; sodium acetate; vanadia; Aliquat 336; In water; at 75 ℃; for 5.5h;

DOI:10.1039/c2gc16328d

Reference yield: 57.0%

acetic anhydride (108-24-7) + Δ9(11)22-isoallospirosten-3β-ol (1106-20-3) → 20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate (21650-83-9)

Guidance literature:

acetic anhydride; Δ⁹⁽¹¹⁾22-isoallospirosten-3β-ol; With pyridine; ammonium chloride; at 125 - 135 ℃;

With chromium(VI) oxide; acetic acid; In water; 1,2-dichloro-ethane; at 20 ℃; for 1h;

With aluminum oxide; In benzene; for 2h;

DOI:10.1080/00397910500464855

Reference yield:

Δ9(11)22-isoallospirosten-3β-ol-12-one-3-acetate (989-73-1) → 20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate (21650-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating

1.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H₂O / 5 h / 195 - 197 °C

2.1: pyridine; ammonium chloride / 125 - 135 °C

2.2: acetic acid; chromium trioxide / H₂O; 1,2-dichloro-ethane / 1 h / 20 °C

2.3: 57 percent / aluminium oxide / benzene / 2 h

With pyridine; ammonium chloride; hydrazine hydrate; In ethylene glycol; 1.1: Wolff-Kishner reduction / 1.2: Wolff-Kishner reduction;

DOI:10.1080/00397910500464855

upstream raw materials:

acetic anhydride

Δ⁹⁽¹¹⁾22-isoallospirosten-3β-ol

Δ⁹⁽¹¹⁾22-isoallospirosten-3β-ol-12-one-3-acetate

hecogenin

Downstream raw materials:

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione

(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2,2-Diiodo-acetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

betamethasone