Epoprostenol

Base Information

• Chemical Name: Epoprostenol
• CAS No.: 35121-78-9
• Deprecated CAS: 63748-50-5,63859-31-4
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• UNII: DCR9Z582X0
• DSSTox Substance ID: DTXSID5022988
• Nikkaji Number: J17.550A
• Wikipedia: Prostacyclin
• Wikidata: Q412050
• NCI Thesaurus Code: C61748
• RXCUI: 8814
• Pharos Ligand ID: QFY18N3QPJ2R
• Metabolomics Workbench ID: 2446
• ChEMBL ID: CHEMBL1139
• Mol file: 35121-78-9.mol

Synonyms:Epoprostanol;Epoprostenol;Epoprostenol Sodium;Epoprostenol Sodium Salt, (5Z,9alpha,11alpha,13E,15S)-Isomer;Flolan;Prostacyclin;Prostaglandin I(2);Prostaglandin I2;Veletri

Chemical Property of Epoprostenol

Chemical Property:

• Vapor Pressure: 1.86E-13mmHg at 25°C
• Refractive Index: 1.611
• Boiling Point: 530.2°Cat760mmHg
• PKA: 4.70±0.10(Predicted)
• Flash Point: 182.1°C
• PSA: 89.82000
• Density: 1.221g/cm³
• LogP: 2.07380
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 485

Purity/Quality:

98%,99%, ^*data from raw suppliers

Epoprostenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)O2)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O)O
• Recent ClinicalTrials: VentaProst in Subjects With COVID-19 Requiring Mechanical Ventilation
• Recent EU Clinical Trials: Combined drug Approach to Prevent Ischemia-reperfusion injury during Transplantation of Livers (CAPITL): a first-in-men study
• Recent NIPH Clinical Trials: ACT-385781A extension study for PAH pediatric patients
• Uses: Inhibitor (platelet). [Names previously used: Prostacyclin, PGI2, Prostagland in I2, Prostaglandin X, PGX].
• Therapeutic Function: Platelet aggregation inhibitor, Antimetastatic

Technology Process of Epoprostenol

There total 6 articles about Epoprostenol 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:

[3aR-[3aα,4α(E),5β,6aα]]-1-(6,6-Difluorohexahydro-2,5-dihydroxy-2H-cyclopenta[b]furan-4-yl)-1-octen-3-one + trimethyl orthoformate (149-73-5) → Epoprostenol (35121-78-9)

Guidance literature:

With hydrogenchloride; sodium borohydrid; In methanol; CeCl₃; water; acetonitrile;

Reference yield:

5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF2α methyl ester (59926-53-3) → Epoprostenol (35121-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Hg(II) trifluoroacetate, N(C₂H₅)3, 2) NaBH₄, NaOMe / 1) THF, -78 deg C, 1 h, 2) THF - MeOH, -78 deg C, 1 h

2: 74 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 15 h / 15 °C

3: alkaline hydrolysis

With sodium tetrahydroborate; Hg(II) trifluoroacetate; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86399-6

Reference yield:

11,15-O-bis(tert-butyldimethylsilyl)PGI2 methyl ester (78824-82-5) → Epoprostenol (35121-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 15 h / 15 °C

2: alkaline hydrolysis

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86399-6

upstream raw materials:

PGI₂ methyl ester

5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF_2α methyl ester

11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester

trimethyl orthoformate

Downstream raw materials:

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid

Refernces

Cross-Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion

10.1002/chem.201901163

The study focuses on the cross-coupling reaction (CCR) of alkenyl sulfoximines and alkenyl aminosulfoxonium salts with organozincs, facilitated by dual nickel catalysis and Lewis acid promotion. The primary chemicals utilized in this research include exocyclic, axially chiral, and acyclic alkenyl (N-methyl)sulfoximines, alkyl- and arylzincs, and Ni(dppp)Cl2 as the precatalyst. MgBr2 was employed as a promoter, and the reactions generally proceeded in ether as the solvent, although THF was also tested. The purpose of these chemicals was to investigate the CCR's effectiveness in producing stereoretentive products, which are crucial for the stereoselective synthesis of exocyclic and axially chiral alkenes. These alkenes are significant in the synthesis of medicinally important prostacyclin analogs such as iloprost, cicaprost, and inter-m-phenylene carbacyclin. The study provides insights into the stereochemical course of the CCR and its application in the synthesis of complex organic molecules with potential pharmaceutical relevance.

Synthesis of 5-Fluoroprostacyclin

10.1021/jo00382a003

The research focuses on the synthesis of 5-fluoroprostacyclin, a stable and potent prostacyclin analogue, which is a significant advancement in the field due to its potential clinical applications as an inhibitor of platelet aggregation. The study aimed to overcome the limitations of prostacyclin's rapid hydration and inactivation by introducing a fluorine atom at the 5- or 7-carbon atom to achieve chemical stabilization. The process involved the reaction of protected prostacyclin derivatives with perchloryl fluoride in methanol, leading to the formation of 5-fluoro-6-methoxy derivatives. These were then separated, identified, and subjected to pyrolysis in the presence of magnesium triflate to yield 5(R)- or 5(S)-fluoro-A6-PGI2 derivatives. The study proposed a mechanism to explain the observed stereospecificity and concluded that the carbon-fluorine bond's stereoelectronic relationship with an adjacent carbonium ion is crucial in determining the product's configuration.