38344-08-0

Basic information

• Product Name: 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA
• Synonyms: 9ALPHA,11ALPHA-15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROSTA-5Z,13E-DIEN-1-OIC ACID;17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA;BIMATOPROST(TM) (FREE ACID);17-phenyl-18,19,20-trinorprostaglandin F2 alpha;(5Z)-7-[(1R)-3α,5α-Dihydroxy-2β-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentan-1α-yl]-5-heptenoic acid;(5Z,13E,15S)-9α,11α,15-Trihydroxy-17-phenyl-18,19,20-trinorprosta-5,13-diene-1-oic acid;(5Z,9α,11α,13E,15S)-9,11,15-Trihydroxy-17-phenyl-18,19,20-trinorprosta-5,13-diene-1-oic acid;17-Phenyl-18,19,20-trinorprostaglandin F2α
• CAS NO: 38344-08-0
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.5
• Product Categories: Aromatics, Chiral Reagents, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 38344-08-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 597.4°Cat760mmHg
• Flash Point: 329.1°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 4.05E-15mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA(CAS DataBase Reference)
• NIST Chemistry Reference: 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA(38344-08-0)
• EPA Substance Registry System: 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA(38344-08-0)

Safety Data

• Hazardous Substances Data: 38344-08-0(Hazardous Substances Data)

Usage

Description

17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA, also known as Bimatoprost Acid, is a member of the prostaglandins Falpha class. It is a metabolically stable analog of PGF2α and serves as an impurity in the antiglaucoma agent Bimatoprost. This white solid is a potent agonist for the FP receptor and is characterized by a double bond at position 13.

Uses

Used in Pharmaceutical Industry:
17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA is used as an impurity in the antiglaucoma agent Bimatoprost for its role in treating glaucoma and ocular hypertension. As a potent agonist for the FP receptor, it helps in reducing intraocular pressure, which is crucial for managing these eye conditions.
Used in Research and Development:
In the field of pharmaceutical research and development, 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA is used as a metabolically stable analog of PGF2α. This allows researchers to study its interactions with the FP receptor and explore its potential applications in developing new drugs for various medical conditions.
Used in Quality Control:
17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA is also used in the quality control of Bimatoprost, ensuring that the final product meets the required standards and is free from harmful impurities. This is essential for maintaining the safety and efficacy of the antiglaucoma agent.

InChI:InChI=1/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18?,19-,20-,21+,22+/m1/s1

Upstream product

• 51014-26-7 (1S,5R,6R,7R)-6-[(E)-3(S)-hydroxy-1-octenyl]-7-(4-phenyl-benzoyloxy)-2-oxabicyclo[3.3.0]octane-3-one 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 856453-32-2 (3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol 
• 41639-74-1 (3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one 
• 69610-63-5 (3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one 
• 856240-62-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 
• 1415393-93-9 [1,1'-biphenyl]-4-carboxylic acid ((3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2-hydroxy-2H-cyclopenta[b]furan-5-yl) ester 
• 41639-73-0 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 1395619-06-3 (3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 1395618-89-9 (3aR,4S,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-(trityloxymethyl)hexahydro-2H-cyclopenta [b] furan-2-one 
• 62939-85-9 (-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 1395618-63-9 (3aR,4S,5R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-5-{[(tert-butyl)(diphenyl)silyl]oxy}-3,3a,5,5,6,6a-hexahydro-2H-cyclopenta[b]furan-2-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 58707-50-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 

Downstream Products

• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 38315-47-8 (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 
• 130209-77-7 15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 130273-87-9 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 38315-47-8 17-Phenyl-18,19,20-trinor-PGF(2α)-methylester 
• 1415394-10-3 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]-5-heptenoic acid 1,3-dioxo-1,3-dihydroisoindol-2-yl ester 
• 1415394-05-6 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]-5-heptenoic acid (2,5-dioxopyrrolidin-1-yl) ester 
• 155206-00-1 bimatoprost 

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.

PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

Process for the synthesis of prostaglandins and intermediates thereof

A process is disclosed for the preparation of prostaglandins of the PGF2α-series, in particular Latanoprost, Bimatoprost and Travoprost, which are active in the treatment of ocular hypertensive conditions and glaucoma. The invention also relates to novel intermediates involved in the synthesis of these prostaglandin-PGF2α derivatives.