3alpha,6alpha-Dihydroxy-5beta-pregnan-20-one

Base Information

• Chemical Name: 3alpha,6alpha-Dihydroxy-5beta-pregnan-20-one
• CAS No.: 570-78-5
• Molecular Formula: C21H34 O3
• Molecular Weight: 334.499
• European Community (EC) Number: 209-333-8
• NSC Number: 50920
• UNII: 617IS2U65V
• DSSTox Substance ID: DTXSID60972491
• Nikkaji Number: J14.709E
• Wikidata: Q27116012
• ChEMBL ID: CHEMBL514852
• Mol file: 570-78-5.mol

Synonyms:3,6-dihydroxy-5alpha-pregnan-20-one;diolone;pregnan-3,6-diol-20-one;pregnan-3,6-diol-20-one, (3alpha,5alpha,6alpha)-isomer;pregnan-3,6-diol-20-one, (3alpha,5alpha,6beta)-isomer;pregnan-3,6-diol-20-one, (3alpha,5beta,6beta)-isomer;pregnan-3,6-diol-20-one, (3beta,5alpha,6alpha)-isomer;pregnan-3,6-diol-20-one, (3beta,5alpha,6beta)-isomer;pregnan-3,6-diol-20-one, (3beta,5beta,6alpha)-isomer;pregnan-3,6-diol-20-one, (3beta,5beta,6beta)-isomer;pregnan-3,6-diol-20-one, (5alpha,6alpha)-isomer;pregnan-3,6-diol-20-one, (5alpha,6beta)-isomer

Chemical Property of 3alpha,6alpha-Dihydroxy-5beta-pregnan-20-one

Chemical Property:

• Boiling Point: 469.7°Cat760mmHg
• Flash Point: 252°C
• PSA: 57.53000
• Density: 1.117g/cm³
• LogP: 3.56600
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 531

Purity/Quality:

99% ^*data from raw suppliers

5β-Pregnan-3α,6α-diol-20-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CC(C4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)C

Technology Process of 3alpha,6alpha-Dihydroxy-5beta-pregnan-20-one

There total 16 articles about 3alpha,6alpha-Dihydroxy-5beta-pregnan-20-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:

3α,6α-diacetoxy-5β-pregnanone-(20) (16826-57-6) → 3α,6α-dihydroxy-5β-pregnan-20-one (570-78-5)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01213a052

Reference yield:

24,24-diphenyl 3α,6α-diacetoxy-5β-cholan-23-ene (4250-62-8) → 3α,6α-dihydroxy-5β-pregnan-20-one (570-78-5)

Guidance literature:

Multistep reaction; (i) NBS, CCl₄, (UV-irradiation), (ii) CrO₃, H₂SO₄, aq. AcOH, (iii) KOH, MeOH;

Reference yield:

methyl hyodeoxycholate (2868-48-6) → 3α,6α-dihydroxy-5β-pregnan-20-one (570-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / Kochen der vom Aether befreiten Reaktionsloesung

2: glacial acetic acid; acetic acid anhydride / Erhitzen des Reaktionsprodukts mit wss.-methanol. NaOH

3: glacial acetic acid

4: tetrachloromethane; N-bromo-succinimide / Irradiation_.Behandeln des Reaktionsprodukts mit siedendem N,N-Dimethyl-anilin und Kochen des Reaktionsprodukts mit Acetanhydrid und Eisessig

5: acetic acid; chloroform; CrO₃ and aqueous acetic acid / 0 °C

6: methanol.KOH

With tetrachloromethane; potassium hydroxide; N-Bromosuccinimide; chloroform; acetic anhydride; acetic acid; toluene;

DOI:10.1021/ja01213a052

upstream raw materials:

3α,6α-diacetoxy-5β-pregnanone-(20)

24,24-diphenyl 3α,6α-diacetoxy-5β-cholan-23-ene

methyl hyodeoxycholate

24,24-diphenyl 3α,6α-dihydroxy-5β-cholan-23-ene

Downstream raw materials:

methylandrostenediol

3α,6α,17α-trihydroxy-5β-pregnan-20-one

3α,6α-dihydroxy-5β-androstan-17-one

3α,6α-dihydroxy-5β-pregnan-20-one-(2,4-dinitro-phenylhydrazone)