Beraprost

Base Information

• Chemical Name: Beraprost
• CAS No.: 88430-50-6
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.499
• UNII: 35E3NJJ4O6
• DSSTox Substance ID: DTXSID7049136
• Nikkaji Number: J372.792K
• Wikipedia: Beraprost
• NCI Thesaurus Code: C76896
• Pharos Ligand ID: B2VHVFYGXSMX
• ChEMBL ID: CHEMBL1207745
• Mol file: 88430-50-6.mol

Synonyms:4-(1,2,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4-methyloct-6-yne-1-enyl)-5-cyclopenta(b)benzofuranyl)butyrate;beraprost;beraprost sodium;TRK 100;TRK-100

Chemical Property of Beraprost

Chemical Property:

• Vapor Pressure: 6.32E-14mmHg at 25°C
• Refractive Index: 1.624
• Boiling Point: 572.1 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 193.1 °C
• PSA: 86.99000
• Density: 1.254 g/cm³
• LogP: 3.28590
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 398.20932405
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

98.0% ^*data from raw suppliers

BERAPROST 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CCC(C)C(C=CC1C(CC2C1C3=CC=CC(=C3O2)CCCC(=O)O)O)O
• Isomeric SMILES: CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)O)O)O
• Recent ClinicalTrials: Efficacy and Safety of Dorner Tablets and Aspirin for Prevention of Arteriosclerosis Progress in Type 2 Diabetes Mellitus Patients
• Recent NIPH Clinical Trials: Efficacy, tolerability, and safety of transition from beraprost to selexipag in patients with pulmonary arterial hypertension.
• Uses: Platelet aggregation inhibitor; stable analog of Prostacyclin. Antithrombotic; vasodilator (peripheral).
• Clinical Use: Beraprost is an oral formulation of a prostacyclin analog for the treatment of early stage pulmonary hypertension as well as early stage PVD.

Technology Process of Beraprost

There total 171 articles about Beraprost 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: 99.0%

methyl (1R*,2R*,3aS*,8bS*)-2,3,3a,8b-tetrahydro-2-hydroxy-1-<(E)-(3S*,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl>-1H-cyclopentabenzofuran-5-butylate → (±)-(1R,2R,3aS,8bS)-2,3,3a,8b-tetrahydro-2-hydroxy-1-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-1H-cyclopenta[b]-benzofuran-5-butanoic acid (88430-50-6)

Guidance literature:

With sodium hydroxide; In methanol; at 30 ℃; for 17h;

DOI:10.1016/S0040-4020(99)00020-4

Reference yield: 92.3%

C25H32O5 → beraprost (88475-69-8,88430-50-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 30 - 35 ℃; Solvent;

Reference yield: 88.0%

C25H32O5 → beraprost 314d (88430-50-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00134

upstream raw materials:

2-methylhex-4-ynoic acid

2-methyl-4-hexynoic acid methyl ester

dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate

3a,8b-cis-dihydro-3H-5,7-dibromocyclopentabenzofuran

Downstream raw materials:

C₃₈H₅₃NO₇S

Refernces

• 1、 -. "Preparation method of beraprost sodium". . . Retrieved 2021/10/05.
• 2、 -. "Beraprost-314d crystals and methods for preparation thereof". Page/Page column 8. . Retrieved 2020/03/18.