7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid

Base Information

• Chemical Name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid
• CAS No.: 20592-20-5
• Molecular Formula: C₂₀H₃₈O₅
• Molecular Weight: 358.519
• Hs Code.: 2918290000
• UNII: LS4GH66FAF
• DSSTox Substance ID: DTXSID80415517
• Nikkaji Number: J1.356.494I
• Wikidata: Q76296781
• Metabolomics Workbench ID: 38729
• ChEMBL ID: CHEMBL36817
• Mol file: 20592-20-5.mol

Synonyms:20592-20-5;13,14-Dihydro PGF-1a;13,14-Dihydro PGF-1alpha;7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid;13,14-Dihydro prostaglandin F1alpha;CHEMBL36817;9alpha,11alpha,15S-Trihydroxy-prostan-1-oic acid;Prostan-1-oic acid, 9,11,15-trihydroxy-, (9alpha,11alpha,15S)-;Dihydro-PGF1;SCHEMBL15698198;DTXSID80415517;CHEBI:172589;HMS3648L19;Prostan-1-oicacid, 9,11,15-trihydroxy-, (9a,11a,15S)-;BDBM50085914;13,14-dihydro Prostaglandin F1 alpha;PD021107;SR-01000946451;J-013447;SR-01000946451-1;(15S)-9alpha,11alpha,15-Trihydroxyprostane-1-oic acid;Prostan-1-oicacid,9,11,15-trihydroxy-,(9a,11a,15s)-;7-[3,5-Dihydroxy-2-(3-hydroxy-octyl)-cyclopentyl]-heptanoic acid;7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-3-hydroxyoctyl)cyclopentyl)heptanoic acid;7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-3-hydroxy-octyl)-cyclopentyl]-heptanoic acid

Chemical Property of 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid

Chemical Property:

• Boiling Point: 542.5±35.0 °C(Predicted)
• PKA: 4.78±0.10(Predicted)
• PSA: 97.99000
• Density: 1.080±0.06 g/cm3(Predicted)
• LogP: 3.49090
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 358.27192431
• Heavy Atom Count: 25
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

13,14-dihydro Prostaglandin F1α ≥99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CCC1C(CC(C1CCCCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](CC[C@H]1[C@@H](C[C@@H]([C@@H]1CCCCCCC(=O)O)O)O)O

Technology Process of 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid

There total 6 articles about 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid 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:

dinoprost (551-11-1) → Dihydro-PGF1alpha (20592-20-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-3-hydroxy-octyl)-cyclopentyl]-heptanoic acid methyl ester (52545-95-6) → Dihydro-PGF1alpha (20592-20-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jm990542v

Reference yield:

(+)-prostaglandin F2α (33854-16-9) → Dihydro-PGF1alpha (20592-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate

2: LiOH / tetrahydrofuran; H₂O / 20 °C

With lithium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; 1: Catalytic hydrogenation / 2: saponification;

DOI:10.1021/jm990542v

upstream raw materials:

dinoprost

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-3-hydroxy-octyl)-cyclopentyl]-heptanoic acid methyl ester

(+)-prostaglandin F_2α

Refernces

• 1、 Wang, Yili,Wos, John A.,Dirr, Michelle J.,Soper, David L.,DeLong, Mitchell A.,Mieling, Glen E.,De, Biswanath,Amburgey, Jack S.,Suchanek, Eric G.,Taylor, Cynthia J.. "Design and synthesis of 13,14-dihydro prostaglandin F(1α) analogues as potent and selective ligands for the human FP receptor". . p. 945 - 952. Retrieved 2007/10/03.