4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one

Base Information

• Chemical Name: 4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one
• CAS No.: 2189-83-5
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• NSC Number: 68279
• DSSTox Substance ID: DTXSID301244331
• Nikkaji Number: J690.753I
• Wikidata: Q27148922
• ChEMBL ID: CHEMBL3137915
• Mol file: 2189-83-5.mol

Synonyms:4beta,5beta-Epoxytestosterone;CHEBI:79788;4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one;2189-83-5;CHEMBL3137915;DTXSID301244331;NSC68279;NSC-68279;Q27148922;(4beta,5beta,17beta)-4,5-Epoxy-17-hydroxyandrostan-3-one

Chemical Property of 4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one

Chemical Property:

• Vapor Pressure: 8.49E-10mmHg at 25°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 545

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC45C3(CCC(=O)C4O5)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@@]45[C@@]3(CCC(=O)[C@@H]4O5)C

Technology Process of 4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one

There total 10 articles about 4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-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: 84.0%

17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (1221910-14-0) → 4,5-Epoxy-testosteron (2189-83-5,6765-87-3,16318-53-9,17503-06-9,17503-07-0,17597-25-0,51154-10-0)

Guidance literature:

With Oxone; ammonium bicarbonate; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/ol801157m

Reference yield: 73.0%

testosterone (58-22-0) → 17β-hydroxy-4β,5-epoxy-5β-androstan-3-one (2189-83-5)

Guidance literature:

With tert.-butylhydroperoxide; lithium hydroxide; In ethanol; for 48h; Ambient temperature;

DOI:10.1139/v82-268

Reference yield: 61.1%

testosterone (58-22-0) → 16α-hydroxytestosterone (63-01-4) + 17β-hydroxy-4β,5-epoxy-5β-androstan-3-one (2189-83-5)

Guidance literature:

With Peroxygenase from Chaetomium globosum; dihydrogen peroxide; In aq. phosphate buffer; acetone; at 20 ℃; pH=7; Enzymatic reaction;

DOI:10.1002/cbic.201600677

upstream raw materials:

testosterone

17β-acetoxy-4β,5β-epoxyandrostan-3-one

testosterone acetate

17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Downstream raw materials:

4-Hydroxy-testosteron

2alpha-Hydroxytestosterone

4-hydroxytestosterone

testosterone

Refernces

• 1、 Bender, Matthias,Schmidtmann, Marc,Rullkoetter, Juergen,Summons, Roger E.,Christoffers, Jens. "Identification of a fossil sterane biomarker in crude oil - An androstane with a modified carbon skeleton". . p. 5934 - 5945. Retrieved 2013/09/23.
• 2、 Nowrouzi, Farhad,Janetzko, John,Batey, Robert A.. "Indium-promoted chemo- and diastereoselective allylation of α,β-epoxy ketones with potassium allyltrifluoroborate". supporting information; experimental part. p. 5490 - 5493. Retrieved 2011/02/27.