3b,15b,17a-Trihydroxy-Pregnenone

Base Information

• Chemical Name: 3b,15b,17a-Trihydroxy-Pregnenone
• CAS No.: 80380-40-1
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• DSSTox Substance ID: DTXSID601259155
• Nikkaji Number: J697.666B
• Metabolomics Workbench ID: 35420
• Mol file: 80380-40-1.mol

Synonyms:3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one;3,15,17-THP-20

Chemical Property of 3b,15b,17a-Trihydroxy-Pregnenone

Chemical Property:

• PSA: 77.76000
• LogP: 2.60100
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 348.23005950
• Heavy Atom Count: 25
• Complexity: 627

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CC(C2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O)O
• Isomeric SMILES: CC(=O)[C@]1(C[C@H]([C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O)O

Technology Process of 3b,15b,17a-Trihydroxy-Pregnenone

There total 24 articles about 3b,15b,17a-Trihydroxy-Pregnenone 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: 91.0%

3β,15β-diacetoxy-17α-hydroxy-5-pregnen-20-one (171980-18-0) → 3β,15β,17α-trihydroxy-5-pregnen-20-one (80380-40-1)

Guidance literature:

With sodium hydroxide; In ethanol; at 40 ℃; for 0.166667h;

DOI:10.1016/0039-128X(95)00169-Q

Reference yield: 66.0%

15β,17α-diacetoxy-3β-hydroxy-5-pregnen-20-one (173324-06-6) → 3β,15β,17α-trihydroxy-5-pregnen-20-one (80380-40-1)

Guidance literature:

With sodium hydroxide; In methanol; for 6h; Heating;

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

Reference yield:

dehydroepiandrosterone (53-43-0) → 3β,15β,17α-trihydroxy-5-pregnen-20-one (80380-40-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / n-BuLi, diisopropylamine / hexane; tetrahydrofuran / -78 °C / 1.) 45 min, 2.) 10 min

2: 1.) m-CPBA, 2.) diethylamine / 1.) CH₂Cl₂, -40 deg C, 1 h, 2.) CCl₄, reflux, 15 min

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / -20 °C / 1.) 2 h, 2.) 16 h

4: 80 percent / aq. H₂SO₄ / tetrahydrofuran / 8.5 h / Ambient temperature

5: 98 percent / pyridine / 16 h / Ambient temperature

6: 75 percent / AgNO₃, N-chlorosuccinimide / tetrahydrofuran; H₂O; acetonitrile / 0.5 h

7: 93 percent / H₂ / Rh/Al / ethanol

8: 1.) (EtO)3P, t-BuONa, O₂, 2.) Ac₂O / 1.) DMF, THF, -25 deg C, 16 h, 2.) pyridine, room temperature, 16 h

9: 91 percent / 2M NaOH / methanol / 0.17 h / 40 °C

With sodium hydroxide; N-chloro-succinimide; n-butyllithium; sulfuric acid; hydrogen; oxygen; acetic anhydride; silver nitrate; diethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate; triethyl phosphite; rhodium on aluminium; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; water; acetonitrile;

DOI:10.1016/0039-128X(95)00193-T

upstream raw materials:

3β,15β-diacetoxy-17α-hydroxy-5-pregnen-20-one

15β,17α-diacetoxy-3β-hydroxy-5-pregnen-20-one

15β-acetoxy-20,20-ethylenedioxy-5-pregnen-3β,17α-diol

15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-4-pregnen-3-one