31753-00-1

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octenyl]-2H-cyclopenta[b]furan-5-yl ester is used as an intermediate in the synthesis of Prostaglandin E2 (P838610). Prostaglandin E2 is the most common and biologically potent of mammalian prostaglandins, playing a significant role in various physiological processes, including inflammation, pain, and fever. [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octenyl]-2H-cyclopenta[b]furan-5-yl ester is utilized in the development of pharmaceuticals targeting these conditions, making it a valuable asset in the pharmaceutical industry.
Used in Research and Development:
[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octenyl]-2H-cyclopenta[b]furan-5-yl ester is also used in research and development for the study of prostaglandin biology and its role in various diseases. Understanding the structure-activity relationships and the mechanisms of action of [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octenyl]-2H-cyclopenta[b]furan-5-yl ester can lead to the discovery of new therapeutic agents and a better understanding of prostaglandin-related pathways.

InChI:InChI=1/C28H30O5/c1-2-3-5-10-22(29)15-16-23-24-17-27(30)32-26(24)18-25(23)33-28(31)21-13-11-20(12-14-21)19-8-6-4-7-9-19/h4,6-9,11-16,23-26H,2-3,5,10,17-18H2,1H3/b16-15+/t23-,24-,25-,26+/m1/s1

Upstream product

• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 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 
• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 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 
• 38754-71-1 Biphenyl-4-carboxylic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 139108-43-3 (3aR,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-vinyl-hexahydro-cyclopenta[b]furan-2-one 
• 139108-47-7 Biphenyl-4-carboxylic acid (3aR,5R,6aS)-2-oxo-4-vinyl-hexahydro-cyclopenta[b]furan-5-yl ester 
• 139108-44-4 (3aR,6aS)-4-Vinyl-tetrahydro-cyclopenta[b]furan-2,5-dione 

Downstream Products

• 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 
• 42743-32-8 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-(3-oxo-octyl)-hexahydro-cyclopenta[b]furan-5-yl ester 
• 39182-59-7 (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 122220-90-0 5α-hydroxy-3α-p-phenylbenzoyloxy-2β-(3-oxo-octanyl)-1α-cyclopentane acetic acid γ-lactone ethylene dithioketal 
• 107615-77-0 9α-11β-dihydroxy-15-oxo-Z-prost-5-ene-1-oic acid 
• 42743-23-7 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E,3S)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 42743-23-7 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E,3R)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 42743-23-7 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 35700-23-3 Carboprost 
• 35700-21-1 U 36384 
• 35700-22-2 (5Z,9α,11α,13E,15R)-15-methyl-9,11,15-trihydroxy-prosta-5,13-diene-1-carboxylic acid methyl ester 

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.

Treatment of inflammation with 15-keto-prostaglandin compounds

A method of treatment of inflammatory diseases which comprises administering, to a subject in need of such treatment, an anti-inflammatorily effective amount of a 15-keto-prostaglandin compound.

Promotion of wound-healing with 15-keto-prostaglandin compounds

A method for promoting healing of wound which comprises administering, to a subject in need of such treatment, a wound-healingly effective amount of a 15-ketoprostaglandin compound.

Treatment of pancreatic disease with 15-keto-prostaglandin compounds

A method of treatment of pancreatic disease which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective in treatment of pancreatic disease.

15-keto-prostaglandin compound for improvement of encephalic function

A method of treatment for improving encephalic function which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective for improvement of encephalic function.

Intramolecular Cycloadditions of Keteniminium Salts. A Practical Asymmetric Synthesis of Prostaglandins

The intramolecular cycloaddition of keteniminium salt 5 derived from (2S,5S)-dimethylpyrrolidine is the key step of a short synthetic route toward prostaglandins.