3beta,25-Dihydroxy-5alpha-cholest-8(14)-en-15-one

Base Information

• Chemical Name: 3beta,25-Dihydroxy-5alpha-cholest-8(14)-en-15-one
• CAS No.: 120185-34-4
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.645
• Nikkaji Number: J457.016B
• Mol file: 120185-34-4.mol

Synonyms:3 beta,25-dihydroxy-5 alpha-cholest-8(14)-en-15-one;3,25-DCEO;3,25-dihydroxycholest-8(14)-en-15-one

Chemical Property of 3beta,25-Dihydroxy-5alpha-cholest-8(14)-en-15-one

Chemical Property:

• Vapor Pressure: 2.28E-14mmHg at 25°C
• Boiling Point: 549.6°Cat760mmHg
• Flash Point: 300.2°C
• PSA: 57.53000
• Density: 1.08g/cm³
• LogP: 5.82670
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 722

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CC(=O)C2=C3CCC4CC(CCC4(C3CCC12C)C)O
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC(=O)C2=C3CC[C@H]4C[C@H](CC[C@@]4([C@H]3CC[C@]12C)C)O

Technology Process of 3beta,25-Dihydroxy-5alpha-cholest-8(14)-en-15-one

There total 5 articles about 3beta,25-Dihydroxy-5alpha-cholest-8(14)-en-15-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:

3β-acetoxy-25-hydroxy-5α-cholest-8(14)-en-15-one (120171-20-2) → 3β,25-dihydroxy-5α-cholest-8(14)-en-15-one (120185-34-4)

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 4h; Yield given;

DOI:10.1021/jm00082a021

Reference yield:

3β-acetoxy-5α-cholest-8(14)-en-15-one (34495-42-6) → 3β,25-dihydroxy-5α-cholest-8(14)-en-15-one (120185-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (CF₃CO)2O, H₂O₂, H₂SO₄, 2.) Et₃N, MeOH

2: 91 percent / Dess-Martin reagent / CH₂Cl₂ / 3 h / 25 °C

3: 71 percent / tetrahydrofuran / 2 h / 0 °C

4: 1.) Hg(OAc)2, 2.) NaBH₄, aq. NaOH / 1.) THF, water, a) 0 deg C, 4 h, b) 25 deg C, 5 h, 2.) THF, 5 min

5: K₂CO₃ / methanol / 4 h / 25 °C

With methanol; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; mercury(II) diacetate; dihydrogen peroxide; potassium carbonate; Dess-Martin periodane; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00082a021

Reference yield:

3β-Acetoxy-24-hydroxy-5α-chol-8(14)-en-15-one (136320-58-6) → 3β,25-dihydroxy-5α-cholest-8(14)-en-15-one (120185-34-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / Dess-Martin reagent / CH₂Cl₂ / 3 h / 25 °C

2: 71 percent / tetrahydrofuran / 2 h / 0 °C

3: 1.) Hg(OAc)2, 2.) NaBH₄, aq. NaOH / 1.) THF, water, a) 0 deg C, 4 h, b) 25 deg C, 5 h, 2.) THF, 5 min

4: K₂CO₃ / methanol / 4 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00082a021

upstream raw materials:

3β-acetoxy-25-hydroxy-5α-cholest-8(14)-en-15-one

3β-acetoxy-5α-cholest-8(14)-en-15-one

3β-Acetoxy-24-hydroxy-5α-chol-8(14)-en-15-one

3β-acetoxy-15-oxo-6α-chol-8(14)-en-24-al