38754-71-1

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester is used as an intermediate in the synthesis of Prostaglandin E2 (P838610), which is the most common and biologically potent of mammalian prostaglandins. Prostaglandins are essential in various physiological processes, including inflammation, blood clotting, and the dilation of blood vessels. They also have potential therapeutic applications in treating a range of conditions, such as cardiovascular diseases, asthma, and other inflammatory disorders.

InChI:InChI=1/C21H18O5/c22-12-17-16-10-20(23)25-18(16)11-19(17)26-21(24)15-8-6-14(7-9-15)13-4-2-1-3-5-13/h1-9,12,16-19H,10-11H2/t16-,17-,18+,19-/m1/s1

Upstream product

• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 139108-47-7 Biphenyl-4-carboxylic acid (3aR,5R,6aS)-2-oxo-4-vinyl-hexahydro-cyclopenta[b]furan-5-yl ester 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 139108-44-4 (3aR,6aS)-4-Vinyl-tetrahydro-cyclopenta[b]furan-2,5-dione 
• 139108-43-3 (3aR,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-vinyl-hexahydro-cyclopenta[b]furan-2-one 

Downstream Products

• 79171-99-6 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester 
• 61188-88-3 4β-<8-Methoxy-4(RS)-methyl-3-oxo-1-(trans)octenyl>-2-oxo-5α-p-phenylbenzoyloxy-3,3aβ,4α,5β,6,6aβ-hexahydro-2H-cyclopentafuran 
• 79171-94-1 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-[(E)-4-(4-chloro-phenoxy)-3-oxo-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 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 
• 79171-91-8 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-m-tolyloxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester 
• 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 
• 41639-23-0 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 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 
• 352276-28-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol 
• 145773-21-3 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 145667-75-0 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 41639-84-3 (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α 
• 41639-83-2 latanoprost acid 
• 145773-22-4 isopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(S)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate 

Relevant academic research and scientific papers

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.

PROCESS FOR THE PREPARATION OF A CHIRAL PROSTAGLANDIN ENOL INTERMEDIATE AND INTERMEDIATE COMPOUNDS USEFUL IN THE PROCESS

The present invention relates to a process for the preparation of a chiral prostaglandin enol intermediate of formula 1, comprising the steps of: separating a compound of formula 16-(R,S)-10 into its diastereomers by fractional crystallisation, reducing t

Preparation method for prostaglandins drug intermediate

The invention discloses a preparation method for (3aR,4R,5R,6aR)-4-aldehyde-hexahydro-2-oxo-2H-cyclopentano[b]furan-5-yl[1,1'-biphenyl]-4-foremate, and belongs to the technical field of the medical intermediate preparation. Compared with a former Pfitzner

He fluorine front row element intermediate preparation method (by machine translation)

The invention discloses he fluorine front row element intermediate, i.e. formula 5 compound preparation method, including the use of biphenyl formyl protected Corey lactone as raw materials, through oxidation, HWE connected side chain, fluorinated, hydrolysis of deprotection step. Preparation method of this invention has the operability is strong, stable process, intermediates for the preparation of white powder, good stability. (by machine translation)

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

PROCESS FOR THE PREPARATION OF TRAVOPROST

The invention relates to a process for the preparation of travoprost of formula(I), comprising that, the compound of formula (II), is stereoselectively reduced, the resulting compound of formula (III), is if desired crystallized, the lactone group of the

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.

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.

IMPROVED PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND ANALOGUES THEREOF

The present invention relates to an improved process for the preparation of prostaglandin and prostaglandin analogues, particularly PGF2α derivatives.

Bimatoprost crystalline form I

The invention provides a novel polymorphic form I of crystalline bimatoprost, method for preparation thereof and new crystalline intermediates in the preparation. This form I of crystalline bimatoprost is used in purification of crude bimatoprost and in storage of bimatoprost as active pharmaceutical intermediate. Use of the physical form of bimatoprost in the manufacture of a medicament is also disclosed.