Cloprostenol

Base Information

• Chemical Name: Cloprostenol
• CAS No.: 54276-21-0
• Deprecated CAS: 53529-41-2,87347-50-0,100786-10-5
• Molecular Formula: C22H29ClO6
• Molecular Weight: 424.922
• European Community (EC) Number: 255-028-8,682-029-4
• UNII: 52EJR3Y9IN,4208238832
• DSSTox Substance ID: DTXSID7048372,DTXSID50860575
• Nikkaji Number: J291.064K
• Wikipedia: Cloprostenol
• Wikidata: Q27076117
• NCI Thesaurus Code: C79571
• Pharos Ligand ID: BYSS7ZXKWYPN
• Metabolomics Workbench ID: 152684
• ChEMBL ID: CHEMBL37853
• Mol file: 54276-21-0.mol

Synonyms:Cloprostenol;Cloprostenol Monosodium Salt;Cloprostenol Sodium;Estrumate;ICI 80,966;ICI-80,966;ICI80,966;Monosodium Salt, Cloprostenol;Oestrophan;Salt, Cloprostenol Monosodium;Sodium, Cloprostenol

Chemical Property of Cloprostenol

Chemical Property:

• Boiling Point: 627.99 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 333.596 °C
• PSA: 110.05000
• Density: 1.321 g/cm³
• LogP: 1.86030
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 424.1652663
• Heavy Atom Count: 29
• Complexity: 551

Purity/Quality:

99% ^*data from raw suppliers

(Z)-7-((1R,2R,3R,5S)-2-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(COC2=CC(=CC=C2)Cl)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](COC2=CC(=CC=C2)Cl)O)C/C=C\CCCC(=O)O)O

Technology Process of Cloprostenol

There total 41 articles about Cloprostenol 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: 44.0%

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1′-biphenyl]-4-carboxylate (54713-44-9) → (+)-cloprostenol (54276-21-0)

Guidance literature:

(3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1′-biphenyl]-4-carboxylate; With potassium carbonate; In methanol; dichloromethane;

With diisobutylaluminium hydride; In dichloromethane; toluene;

(4-carboxybutyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; stereoselective reaction;

DOI:10.1039/d1sc03237b

Reference yield:

4-((E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-((Z)-7-isopropoxy-7-oxohept-2-enyl)cyclopentane-1,3-diyl dibenzoate → cloprostenol (40665-92-7,40665-93-8,54276-21-0,54276-22-1,54324-21-9,54324-22-0,54383-10-7,57759-74-7,57759-75-8,57968-81-7,59685-86-8,59685-88-0,72029-43-7,72029-46-0,123750-37-8) + 16-(m-chlorophenoxy)-9α,11α,15β-trihydroxy-17,18,19,20-tetranor-5-cis-13-trans-prostadienoic acid (40665-92-7,40665-93-8,54276-21-0,54276-22-1,54324-21-9,54324-22-0,54383-10-7,57759-74-7,57759-75-8,57968-81-7,59685-86-8,59685-88-0,72029-43-7,72029-46-0,123750-37-8)

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 5h; Inert atmosphere;

DOI:10.2174/157017811795371485

Reference yield:

4-((E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-((Z)-7-isopropoxy-7-oxohept-2-enyl)cyclopentane-1,3-diyl dibenzoate → cloprostenol (40665-92-7,40665-93-8,54276-21-0,54276-22-1,54324-21-9,54324-22-0,54383-10-7,57759-74-7,57759-75-8,57968-81-7,59685-86-8,59685-88-0,72029-43-7,72029-46-0,123750-37-8) + 16-(m-chlorophenoxy)-9α,11α,15β-trihydroxy-17,18,19,20-tetranor-5-cis-13-trans-prostadienoic acid (40665-92-7,40665-93-8,54276-21-0,54276-22-1,54324-21-9,54324-22-0,54383-10-7,57759-74-7,57759-75-8,57968-81-7,59685-86-8,59685-88-0,72029-43-7,72029-46-0,123750-37-8)

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 5h; Inert atmosphere;

DOI:10.2174/157017811795371485

upstream raw materials:

4-carboxybutyliden triphenylphosphorane sodium

(3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

cloprostenol

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

Downstream raw materials:

cloprostenol

Refernces

• 1、 Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu. "Concise, scalable and enantioselective total synthesis of prostaglandins". . p. 692 - 697. Retrieved 2021/06/01.
• 2、 Mudduluru, Harikrishna,Hindupur, Rama M.,Dubey, Pramod K.,Madhavaram, Shankar,Tatini, Lakshmikumar,Subbaraju, Gottumukkala V.. "Synthesis of (±) travoprost and its analogs". experimental part. p. 234 - 241. Retrieved 2012/04/18.