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

Chemical Properties

White Solid

Uses

Bimatoprost Acid is an impurity of the antiglaucoma agent Bimatoprost (B386820).Bimatoprost Acid is a metabolically stable analog of PGF2α (P838625) and is a potent agonist for the FP receptor.

Definition

ChEBI: A member of the class of prostaglandins Falpha that is latanoprost free acid with a double bond at position 13.

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

• 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 
• 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 
• 130273-87-9 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 130209-77-7 15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 

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.

NOVEL PROCESSES FOR THE PREPARATION OF PROSTAGLANDIN AMIDES

The subject of the invention is process for the preparation of the prostaglandin amides of the general formula I, - where in the formula the bonds marked with dotted lines may be single or double bonds, in the case of double bounds at positions 5,6 and 13,14 they may be in cis or in trans orientation, Q stands for a hydroxyl-group and Z stands for a hydroxyl- or oxo-group, R1 and R2 independently represent hydrogen atom or a straight or branched C1-10 alkyl- or aralkyl- group, optionally substituted with -ONO2 group, or an aralkyl- or aryl- group, which contains heteroatom, R3 represents a straight or branched, saturated or unsaturated C4-6 hydrocarbon group, or a C4-10 alkylcycloalkyl- or cycloalkyl- group, or an optionally with alkyl group or halogen atom substituted phenyl-, C7-10 alkylaryl- or hetaryl- group, Y represents (CH2)n group or 0 atom or S atom, and where n=0-3.