(Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER
• CAS No.: 38315-47-8
• Molecular Formula: C24H34O5
• Molecular Weight: 402.531
• Mol file: 38315-47-8.mol

Synonyms:(Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER;(Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER;17-phenyl trinor Prostaglandin F2α methyl ester;BiMatoprost Acid Methyl Ester

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 2.98E-13mmHg at 25°C
• Boiling Point: 557.2°C at 760 mmHg
• PKA: 14.25±0.20(Predicted)
• Flash Point: 184°C
• PSA: 86.99000
• Density: 1.17g/cm³
• LogP: 3.18380

Purity/Quality:

98% ^*data from raw suppliers

17-phenyl trinor Prostaglandin F2α methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Bimatoprost Acid Methyl Ester is an impurity of the antiglaucoma agent Bimatoprost (B386820).

Technology Process of (Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

There total 18 articles about (Z)-7-[(1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(S)-3-HYDROXY-5-PHENYL-PENT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER 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: 98.0%

(5Z)-bimatoprost acid (38344-08-0) + methyl iodide (74-88-4) → (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester (38315-47-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 4 ℃; for 4h;

Reference yield: 76.0%

C24H32O5 (1243274-57-8) → (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester (38315-47-8)

Guidance literature:

C₂₄H₃₂O₅; With 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride; In toluene; at -70 - 20 ℃;

With hydrogenchloride; In water; toluene;

Reference yield:

1-bromo-4-phenylbutan-2-one (31984-10-8) → (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester (38315-47-8)

Guidance literature:

Multi-step reaction with 6 steps

1: acetonitrile / 3 h / 65 °C / Inert atmosphere

2: lithium hydroxide monohydrate / tert-butyl methyl ether / 0.75 h / 5 °C / Inert atmosphere

3: Candida antarctica lipase B / aq. phosphate buffer / pH 7 - 7.5 / Inert atmosphere

4: diisobutylaluminium hydride / tetrahydrofuran / Inert atmosphere

5: potassium tert-butylate / tetrahydrofuran / 5 °C / Inert atmosphere

6: potassium carbonate / acetone / 16 h / 30 °C / Inert atmosphere

With Candida antarctica lipase B; lithium hydroxide monohydrate; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; aq. phosphate buffer; tert-butyl methyl ether; acetone; acetonitrile; 2: |Wittig-Horner Reaction / 5: |Wittig Olefination;

DOI:10.14233/ajchem.2017.20878

upstream raw materials:

17-Phenyl-18,19,20-trinor-PGF(2α)

methyl iodide

diazomethane

(5Z)-bimatoprost acid

Downstream raw materials:

Acetic acid (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-(S)-3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enyl ester

bimatoprost

Acetic acid (Z)-7-[(1R,2R,3R)-3-hydroxy-2-((E)-(S)-3-hydroxy-5-phenyl-pent-1-enyl)-5-oxo-cyclopentyl]-hept-5-enyl ester

Refernces

• 1、 Kamidi, Vijendhar,Kale, Pooja,Boodida, Sathyanarayana. "A new synthetic approach to prostaglandin analogues: Synthesis of bimatoprost via lipase enzymatic catalysis". . p. 2767 - 2770. Retrieved 2017/11/10.
• 2、 -. "PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS". Paragraph 0279; 0280; 0281; 0282. . Retrieved 2015/02/25.