54276-21-0

Basic information

• Product Name: (+)-Cloprostenol
• Synonyms: (+)-9ALPHA,11ALPHA,15-TRIHYDROXY-16-(3-CHLOROPHENOXY)-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID;(+)-16-M-CHLOROPHENOXY TETRANOR PROSTAGLANDIN F2ALPHA;Superphan;(5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid;(+)-Cloprostenol;cGMP Superphan
• CAS NO: 54276-21-0
• Molecular Formula: C₂₂H₂₉ClO₆
• Molecular Weight: 424.92
• Mol File: 54276-21-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 627.99 °C at 760 mmHg
• Flash Point: 333.596 °C
• Appearance: /
• Density: 1.321
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: (+)-Cloprostenol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Cloprostenol(54276-21-0)
• EPA Substance Registry System: (+)-Cloprostenol(54276-21-0)

Safety Data

• Hazardous Substances Data: 54276-21-0(Hazardous Substances Data)

Usage

General Description

(+)-Cloprostenol is a synthetic prostaglandin analogue that is commonly used in veterinary medicine to induce luteolysis, or the regression of the corpus luteum, in animals such as cows and horses. It is a potent and selective agonist for the prostaglandin F2α receptor, which leads to the contraction of the smooth muscle of the uterus and the subsequent shedding of the uterine lining. This makes it useful in reproductive management, including controlling the estrous cycle, inducing abortion, and treating conditions such as pyometra and endometritis in animals. Additionally, (+)-Cloprostenol has been researched for its potential use in human medicine, particularly in the treatment of conditions such as glaucoma.

Upstream product

• 41723-91-5 4-carboxybutyliden triphenylphosphorane sodium 
• 89560-44-1 (3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol 
• 53872-62-1 [3aα,4α(E),5β,6aα]-(+/-)-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-hexahydro-5-hydroxy-2H-cyclopenta[b]-furan-2-one 
• 40665-94-9 dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 54713-44-9 (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 
• 129098-54-0 (S)-2-(3-chloro-phenoxymethyl)-oxirane 
• 53906-54-0 (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 54324-79-7 (3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 

Downstream Products

• 206555-98-8 cloprostenol 
• 56687-85-5 methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate 

Relevant articles and documents

A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.

An improved and efficient process for the preparation of (+)-cloprostenol

Abstract An improved and efficient synthesis of (+)-cloprostenol has been accomplished in nine steps and 26% overall yield from commercially available (-)-Corey lactone 4-phenylbenzoate alcohol 1. The present route avoids tedious purifications and require

The tetrahydropyranyl-protected mandelic acid: A novel versatile chiral derivatising agent

A simple synthesis of (2R)-2-phenyl-2-[(2S)-tetrahydro-2- pyranyloxy]ethanoic acid, a versatile chiral derivatising agent (CDA), is proposed. The derivatisation of secondary alcohols aimed at the absolute configurational assignment, determination of enantiomeric purity as well as semipreparative resolution is described.