40695-33-8

Basic information

• Product Name: rel-[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
• Synonyms: rel-[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;TV-BPK (Travoprost);(E)-2-Oxo-4-(3-oxo-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-;(E)-2-Oxo-4-(3-oxo-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan;(E)-2-Oxo-4-(3-oxo-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1-biphenyl]-4-carboxylate
• CAS NO: 40695-33-8
• Molecular Formula: C31H25F3O6
• Molecular Weight: 550.5218096
• Mol File: 40695-33-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 128-129 ºC
• Boiling Point: 699.684 °C at 760 mmHg
• Flash Point: 362.651 °C
• Appearance: /
• Density: 1.37
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: 2-8°C
• CAS DataBase Reference: rel-[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(CAS DataBase Reference)
• NIST Chemistry Reference: rel-[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(40695-33-8)
• EPA Substance Registry System: rel-[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(40695-33-8)

Safety Data

• Hazardous Substances Data: 40695-33-8(Hazardous Substances Data)

Usage

Description

rel-[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 is a complex synthetic compound characterized by a biphenyl core structure and a carboxylic acid group. It features a hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester moiety and exhibits specific stereochemistry due to the presence of stereocenters at the 3a, 4, 5, and 6a positions. rel-[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 holds potential for various applications in fields such as pharmaceuticals, materials science, and organic chemistry, making it a subject of interest for further research and development.

Uses

Used in Pharmaceutical Industry:
rel-[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 is used as a potential pharmaceutical agent for its unique structural and stereochemical properties, which may contribute to the development of new drugs with novel mechanisms of action.
Used in Materials Science:
In the field of materials science, rel-[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 is utilized for its potential to create new materials with specific properties, such as improved stability or reactivity, due to its complex structure and stereochemistry.
Used in Organic Chemistry Research:
rel-[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 serves as a subject of study in organic chemistry research, where its synthesis, properties, and reactions can provide insights into the development of new synthetic methods and understanding of molecular behavior.

InChI:InChI=1/C31H25F3O6/c32-31(33,34)22-7-4-8-24(15-22)38-18-23(35)13-14-25-26-16-29(36)39-28(26)17-27(25)40-30(37)21-11-9-20(10-12-21)19-5-2-1-3-6-19/h1-15,25-28H,16-18H2/b14-13+/t25-,26-,27-,28+/m1/s1

Upstream product

• 54094-19-8 dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 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 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 588-26-1 methyl 2-[3-(trifluoromethyl)phenoxy]acetate 
• 98-17-9 3-Trifluoromethylphenol 

Downstream Products

• 1444103-94-9 [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-hydroxy-2H-cyclopenta[b]furan-5-yl ester 
• 1444103-96-1 [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-hydroxy-2H-cyclopenta[b]furan-5-yl ester 
• 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 
• 54276-17-4 (+)-fluprostenol 
• 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 

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.

Preparation method of Prostaglandin Intermediate

In the present invention, provided is a manufacturing method of a prostaglandin intermediate, which comprises a step of manufacturing an intermediate represented by chemical formula III-1 or III-2 from Corey lactone aldehyde represented by chemical formul

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

Provided herein is an improved, commercially viable and industrially advantageous process for the preparation of a prostaglandin derivatives and intermediates thereof, in high yield and purity.