5alpha-Pregnan-20-one, 3alpha,11beta-dihydroxy-

Base Information

• Chemical Name: 5alpha-Pregnan-20-one, 3alpha,11beta-dihydroxy-
• CAS No.: 23930-29-2
• Molecular Weight: 334.49
• DSSTox Substance ID: DTXSID301275594
• Nikkaji Number: J121.984G
• ChEMBL ID: CHEMBL2322582
• Mol file: 23930-29-2.mol

Synonyms:23930-29-2;3alpha,11beta-Dihydroxy-5alpha-pregnan-20-one;5.alpha.-Pregnan-20-one, 3.alpha.,11.beta.-dihydroxy-;Pregnan-20-one, 3,11-dihydroxy-, (3.alpha.,5.alpha.,11.beta.)-;1-[(3R,5S,8S,9S,10S,11S,13S,14S,17S)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone;3,11-Dihydroxypregnan-20-one;3,11-Dihydroxypregnan-20-one #;CHEMBL2322582;SCHEMBL11440482;NFVCQZNBRFPYOP-DAVHWALQSA-N;DTXSID301275594;3a,11b-di-hydroxy-5a-pregnan-20-one;(3alpha,5alpha,11beta)-3,11-Dihydroxypregnan-20-one

Chemical Property of 5alpha-Pregnan-20-one, 3alpha,11beta-dihydroxy-

Chemical Property:

• 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:

3α,11β-Dihydroxy-5α-pregnan-20-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CC(C3C2CCC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: 3α,11β-Dihydroxy-5α-pregnan-20-one is a metabolite of progesterone (P755900). Progesterone is a cholesterol derived hormone which is critical for pregnancy. Progesterone is an immunomodulatory female sex steroid.

Technology Process of 5alpha-Pregnan-20-one, 3alpha,11beta-dihydroxy-

There total 18 articles about 5alpha-Pregnan-20-one, 3alpha,11beta-dihydroxy- 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:

20,20-ethylenedioxy-5α-pregnane-3α,11β-diol (23930-32-7) → 5α-pregnan-3α,11β-diol-20-one (23930-29-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 55 ℃; for 0.25h;

DOI:10.1021/jm3016365

Reference yield:

3β-acetoxy-5α-pregnane-11,20-dione (3684-81-9) → 5α-pregnan-3α,11β-diol-20-one (23930-29-2)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / methanol; water / 1 h / Reflux

2: pyridine / 2 h / 0 °C

3: potassium nitrite / N,N-dimethyl-formamide / 130 °C

4: toluene-4-sulfonic acid

5: lithium aluminium tetrahydride / tetrahydrofuran

6: toluene-4-sulfonic acid / acetone / 0.25 h / 55 °C

With pyridine; lithium aluminium tetrahydride; potassium nitrite; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm3016365

Reference yield:

Alphaxalone (23930-19-0) → 5α-pregnan-3α,11β-diol-20-one (23930-29-2)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid

2: lithium aluminium tetrahydride / tetrahydrofuran

3: toluene-4-sulfonic acid / acetone / 0.25 h / 55 °C

With lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone;

DOI:10.1021/jm3016365

upstream raw materials:

20,20-ethylenedioxy-5α-pregnane-3α,11β-diol

3β-acetoxy-5α-pregnane-11,20-dione

Alphaxalone

(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-11-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Refernces