3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone

Base Information

• Chemical Name: 3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone
• CAS No.: 13934-61-7
• Molecular Formula: C22H32O3
• Molecular Weight: 344.494
• European Community (EC) Number: 237-709-1
• DSSTox Substance ID: DTXSID701156079
• Nikkaji Number: J24.248I
• Mol file: 13934-61-7.mol

Synonyms:13934-61-7;3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone;EINECS 237-709-1;SCHEMBL18218190;DTXSID701156079;Pregn-5-ene-21-carboxylic acid, 3,17-dihydroxy-, gamma-lactone, (3beta,17alpha)-

Chemical Property of 3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 639

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1=CCC3C2CCC4(C3CCC45CCC(=O)O5)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)O

Technology Process of 3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone

There total 12 articles about 3beta,17alpha-Dihydroxypregn-5-ene-21-carboxylic acid gamma-lactone 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%

C28H46O3Si → 3β,17β-Dihydroxy-5-androsten-17α-propanoic Acid γ-Lactone (13934-61-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.2174/0929867321666140601164240

Reference yield: 83.0%

21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne (156894-83-6) → 3β,17β-Dihydroxy-5-androsten-17α-propanoic Acid γ-Lactone (13934-61-7)

Guidance literature:

21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

With Trimethyl borate; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.orglett.1c00840

Reference yield: 78.0%

Allyl Tetramethylphosphorodiamidate (50775-60-5) + 3-tetrahydropyran-2-yloxy-androst-5-en-17-one (19637-35-5) → 3β,17β-Dihydroxy-5-androsten-17α-propanoic Acid γ-Lactone (13934-61-7)

Guidance literature:

With hydrogenchloride; n-butyllithium; hexane; 1.) THF, reflux, 7 h, 2.) methanol, 40 degC, 2 h;

DOI:10.1055/s-1980-28994

upstream raw materials:

Allyl Tetramethylphosphorodiamidate

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne

dehydroepiandrosterone

Downstream raw materials:

3β-tosyloxy-17α-pregn-5-ene-21,17-carbolactone

canrenone

SPIRONOLACTONE

C₂₂H₃₂BrClO₃

Refernces

• 1、 Hess,H.-J.. "". . p. 1096 - 1098. Retrieved 1962.
• 2、 Thiele,Rabe,Hessenkemper,Roell,Bartsch,Kraft,Abraham,Houtsmuller,Van Royen,Giannis,Baniahmad. "Novel nor-homo-and spiro-oxetan- steroids target the human androgen receptor and act as antiandrogens". . p. 1156 - 1167. Retrieved 2015/06/22.