54324-79-7

Usage

Uses

Used in Medicinal Chemistry:
[1,1'-Biphenyl]-4-carboxylic acid [3aR-[3aa,4a(E),5b,6aa]]-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester is used as a building block for the design and synthesis of novel pharmaceutical compounds. Its unique structure and potential biological activity make it a promising candidate for the development of new therapeutic agents.
Used in Drug Development:
In the pharmaceutical industry, [1,1'-Biphenyl]-4-carboxylic acid [3aR-[3aa,4a(E),5b,6aa]]-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester is utilized for the discovery and optimization of new drug candidates. Its specific stereochemistry and functional groups can be leveraged to modulate the pharmacological properties of the resulting compounds, potentially leading to the development of more effective and targeted therapies.

Upstream product

• 40665-94-9 dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 108-43-0 3-monochlorophenol 
• 52094-98-1 ethyl (3-chlorophenoxy)acetate 
• 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 

Downstream Products

• 54294-93-8 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-4-(3-chloro-phenoxy)-3-hydroxy-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 54713-44-9 (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1′-biphenyl]-4-carboxylate 
• 53906-54-0 (3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 79124-66-6 N-(methanesulfonyl)-16-(m-chlorophenoxy)-ω-tetranor-PGE₂-carboxamide 
• 324763-89-5 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 
• 101915-58-6 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 54276-21-0 (+)-cloprostenol 
• 109323-20-8 (3aR,4R,5R,6aS)-4-((3R,E)-4-(3-chlorophenoxy)-3-(1-ethoxyethoxy)but-1-enyl)-5-(1-ethoxyethoxy)hexahydro-2Hcyclopenta[b]furan-2-ol 

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.

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

N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants

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).