methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

Base Information

• Chemical Name: methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
• CAS No.: 56687-85-5
• Molecular Formula: C23H31ClO6
• Molecular Weight: 438.949
• Mol file: 56687-85-5.mol

Synonyms:methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate;56687-85-5;5-Heptenoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, methyl ester, (1R-(1-alpha(Z),2-beta(1E,3R*),3-alpha,5-alpha))-;C23H31ClO6;C23-H31-Cl-O6;LS-74575

Chemical Property of methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

Chemical Property:

• Vapor Pressure: 1.5E-14mmHg at 25°C
• Boiling Point: 585.5°C at 760 mmHg
• PKA: 13.41±0.20(Predicted)
• Flash Point: 307.9°C
• PSA: 96.22000
• Density: 1.264g/cm³
• LogP: 3.28340
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 438.1809164
• Heavy Atom Count: 30
• Complexity: 566

Purity/Quality:

≥98% ^*data from raw suppliers

(+)-Cloprostenol methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC(=CC=C2)Cl)O)O)O
• Isomeric SMILES: COC(=O)CCC/C=C\CC1[C@H](C(CC1O)O)/C=C/C(COC2=CC(=CC=C2)Cl)O
• Description: (+)-Cloprostenol is a synthetic analog of prostaglandin F2α (PGF2α). It is an FP receptor agonist and a potent luteolytic agent in rats and hamsters. It is 200 times and 100 times more potent than PGF2α in terminating pregnancy in hamsters and rats, respectively, without the side effects associated with PGF2α. Cloprostenol is also used in veterinary medicine as a luteolytic agent for the induction of estrus and the treatment of reproductive disorders in cattle, swine, and horses. (+)-Cloprostenol methyl ester is a more lipid soluble form of cloprostenol, which may be more amenable for certain formulations.

Technology Process of methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate

There total 10 articles about methyl (Z)-7-[(2R)-2-[(E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate 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: 77.0%

(+)-cloprostenol (54276-21-0) + methyl iodide (74-88-4) → methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate (56687-85-5)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 20h;

DOI:10.1016/j.mencom.2017.03.005

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate (56687-85-5)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂SO₄

2: MeONa / methanol

3: (COCl)2, NEt₃ / dimethylsulfoxide

4: 50percent aq. NaOH, BuNEt₃Cl / CH₂Cl₂

5: (i-Bu)2Al-O-C₆H₂-(2,6-di-t-Bu,4-Me) / CH₂Cl₂ / -78 °C

6: (i-Bu)2AlH

With sodium hydroxide; oxalyl dichloride; sulfuric acid; sodium methylate; triethylbutylammonium chloride; diisobutylaluminium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+)-cloprostenol (54276-21-0) → methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate (56687-85-5)

Guidance literature:

upstream raw materials:

diazomethane

(+)-cloprostenol

methanol

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F_1α methyl ester

(E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester

(2E,5E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid methyl ester

16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

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