15(R)-ILOPROST

Base Information

• Chemical Name: 15(R)-ILOPROST
• CAS No.: 85026-51-3
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.494
• Mol file: 85026-51-3.mol

Synonyms:6,9ALPHA-METHYLENE-11ALPHA,15R-DIHYDROXY-16-METHYL-PROSTA-5E,13E-DIEN-18-YN-1-OIC ACID;

Chemical Property of 15(R)-ILOPROST

Chemical Property:

• PSA: 77.76000
• LogP: 3.54130

Purity/Quality:

99% ^*data from raw suppliers

15(R)-Iloprost ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Iloprost is a second generation structural analog of prostacyclin (PGI2) with about ten-fold greater potency than the first generation stable analogs, typified by carbaprostacyclin. Iloprost binds with equal affinity to the recombinant human IP and EP receptors with a Ki of 11 nM. 15(R)-Iloprost is the “unnatural” or inverted C-15 epimer of iloprost. This transformation frequently attenuates the biological agonist activity of prostaglandin analogs by several orders of magnitude. There are no literature reports of the biological activity of 15(R)-iloprost.

Technology Process of 15(R)-ILOPROST

There total 10 articles about 15(R)-ILOPROST 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:

5-[(3aS,5R,6aS)-4-[(E)-(S)-4-Methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-en-6-ynyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid (79745-58-7,81338-61-6,81338-62-7,81338-63-8,81339-64-2) → 5-[(3aS,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid (74843-13-3,74843-14-4,74843-29-1,74843-30-4,78919-13-8,82889-99-4,85026-51-3)

Guidance literature:

Reference yield:

5-[(3aS,5R,6aS)-4-[(E)-(S)-4-Methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-en-6-ynyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid (79745-58-7,81338-61-6,81338-62-7,81338-63-8,81339-64-2) → iloprost (74843-13-3,74843-14-4,74843-29-1,74843-30-4,78919-13-8,82889-99-4,85026-51-3)

Guidance literature:

Reference yield:

4-carboxybutyliden triphenylphosphorane sodium (41723-91-5) → 5-[(3aS,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid (74843-13-3,74843-14-4,74843-29-1,74843-30-4,78919-13-8,82889-99-4,85026-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO, 45 deg C

upstream raw materials:

5-[(3aS,5R,6aS)-4-[(E)-(S)-4-Methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-en-6-ynyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid

4-carboxybutyliden triphenylphosphorane sodium

(3aS,5R,6aR)-5-Hydroxy-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-2-one

(3aS,5R,6aR)-4-[(E)-(S)-4-Methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-en-6-ynyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-2-one