53872-60-9

Basic information

• Product Name: (+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE
• Synonyms: Travoprost Epoxide;(3aR,4R,5R,6aS)-5-Hydroxy-4-((R,E)-3-hydroxy-4-(3-(trifluoroMethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one;Fluprostenone Lactone Diol;Anti-TERT antibody produced in goat;EST2;TCS1;TRT;Anti-Telomerase antibody produced in rabbit
• CAS NO: 53872-60-9
• Molecular Formula: C₁₈H₁₉F₃O₅
• Molecular Weight: 372.34
• Mol File: 53872-60-9.mol

Chemical Properties

• Boiling Point: 520.599 °C at 760 mmHg
• Flash Point: 268.649 °C
• Appearance: /
• Density: 1.434 g/cm³
• Refractive Index: 1.583
• Storage Temp.: -20°C
• PKA: 13.34±0.20(Predicted)
• CAS DataBase Reference: (+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE(53872-60-9)
• EPA Substance Registry System: (+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE(53872-60-9)

Safety Data

• Hazardous Substances Data: 53872-60-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one is used as an intermediate in the synthesis of prostaglandin derivatives. Prostaglandins are a group of naturally occurring lipid compounds that have various physiological effects, including the regulation of blood flow, inflammation, and pain. (+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one's unique structure makes it a valuable building block for the development of new pharmaceuticals targeting these physiological processes.
Used in Chemical Research:
Due to its complex structure and functional groups, (+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one can also be used as a research tool in the field of organic chemistry. It can serve as a starting material for the synthesis of various other complex molecules, enabling scientists to explore new chemical reactions and mechanisms.

InChI:InChI=1/C18H19F3O5/c19-18(20,21)10-2-1-3-12(6-10)25-9-11(22)4-5-13-14-7-17(24)26-16(14)8-15(13)23/h1-6,11,13-16,22-23H,7-9H2/b5-4+/t11-,13-,14-,15-,16+/m1/s1

Upstream product

• 98-17-9 3-Trifluoromethylphenol 
• 588-26-1 methyl 2-[3-(trifluoromethyl)phenoxy]acetate 
• 1056147-98-8 (3aR,4R,5R,6aS)-4-((E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)-2oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 54142-64-2 [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 54094-19-8 dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate 
• 114488-91-4 [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 

Downstream Products

• 1240483-24-2 (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R,E)-3-((tert-butyldimethylsilyl)oxy)-4-(3-(trifluoromethyl)-phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 1204185-88-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 
• 340181-93-3 travoprost 
• 1300093-06-4 (Z)-isopropyl 7-((1R,2R,3R,5S)-5-hydroxy-3-((2-methoxyethoxy)methoxy)-2-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate 
• 1300093-04-2 (Z)-7-((1R,2R,3R,5S)-5-hydroxy-3-((2-methoxyethoxy)methoxy)-2-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoic acid 
• 1300093-03-1 (3aR,4R,5R,6aS)-5-((2-methoxyethoxy)methoxy)-4-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-ol 
• 1300093-02-0 (3aR,4R,5R,6aS)-5-((2-methoxyethoxy)methoxy)-4-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 79124-64-4 N-(methanesulfonyl)-16--ω-tetranor-PGE₂-carboxamide 
• 208252-64-6 (3aR,4R,5R,6aS)-5-((tetrahydro-2H-pyran-2-yl)oxy)-4-((3R,E)-3-((tetrahydro-2H-pyran-2-yl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol 
• 208180-17-0 (3aR,4R,5R,6aS)-5-((tetrahydro-2H-pyran-2-yl)oxy)-4-((3R,E)-3-((tetrahydro-2H-pyran-2-yl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 

Relevant articles and documents

Novel method for preparing Prostaglandin derivatives

Provided is a novel method for preparing prostaglandin derivatives. The method is suitable for mass production by effectively manufacturing prostaglandin derivatives with high yield. The method comprises the following steps: (S-1) adding a first reducing agent to a prostaglandin intermediate compound represented by chemical formula II and manufacturing a compound represented by chemical formula III; (S-2) manufacturing a compound represented by chemical formula IV from the compound represented by chemical formula III in the presence of a base; (S-3) adding a second reducing agent to the compound represented by chemical formula IV and manufacturing a compound represented by chemical formula V; and (S-4) performing Wittig reaction of the compound represented by chemical formula V and a compound represented by chemical formula VI, and manufacturing a compound represented by chemical formula I.COPYRIGHT KIPO 2017

AN IMPROVED AND SCALABLE PROCESS FOR PREPARATION OF PROSTAGLANDIN DERIVATIVES AND INTERMEDIATES THEREOF

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A NOVEL PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND INTERMEDIATES THEREOF

This invention relates to novel process for the preparation of prostaglandin compounds having formula (K), wherein R is selected from the group consisting of C1-C7 alkyl; C7-C17 aralkyl wherein the aryl group is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and (CH2)nOR2 wherein n is from 1 to 3 and R2 represents a C6-C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and R1 is selected from OR3 and NHR3 wherein R3 is C1-C6 alkyl, H; and dashed lines represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.

PROCESS FOR THE PREPARATION OF F-SERIES PROSTAGLANDINS

A process for the synthesis and purification of F-series prostaglandin compounds and synthetic intermediates used to prepare them. The synthetic intermediates are solid and may be purified by precipitation and therefore may form the representative F-series prostaglandin compounds such as latanoprost, bimatoprost, fluprostenol, cloprostenol, and substituted analogs therefrom in highly pure forms.

Processes and intermediates for the preparations of prostaglandins

The present invention provides novel processes for the preparation of a cyclopentanone of Formula II and a lactone of Formula I, which are useful in the production of prostaglandins: wherein Z, R2, R3, X1, X2, and are as defined in the specification. The invention also provides novel enantiomerically enriched compounds.

Processes and intermediates for the preparations of prostaglandins

The present invention provides novel processes for the preparation of a cyclopentanone of Formula II and a lactone of Formula I, which are useful in the production of prostaglandins: wherein Z, R2, R3, X1, X2, and ------------ are as defined in the specification. The invention also provides novel enantiomerically enriched compounds.

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In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro and in vivo models.Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).