51014-26-7

Basic information

• Product Name: [1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester
• Synonyms: [1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester;[1,1'-Biphenyl]-4-carboxylic acid, hexahydro-4-(3-hydroxy-1-octenyl)-2-oxo-2H-cyclopenta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3S*),5b,6aa]]-;3aR,4R,5R,6aS)-Hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1'-Biphenyl]-4-carboxylic Acid;[1,1'-Biphenyl]-4-carboxylic acid (3aR, 4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-;VUHYYFILFMCYQI-QCRMGOLMSA-N
• CAS NO: 51014-26-7
• Molecular Formula: C₂₈H₃₂O₅
• Molecular Weight: 449
• Mol File: 51014-26-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: DCM, Ethyl Acetate
• CAS DataBase Reference: [1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester(51014-26-7)
• EPA Substance Registry System: [1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester(51014-26-7)

Safety Data

• Hazardous Substances Data: 51014-26-7(Hazardous Substances Data)

Usage

Uses

[1,1''-Biphenyl]-4-carboxylic Acid (3aR,4R,5R,6aS)-Hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl Ester is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.

Upstream product

• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 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 
• 31753-00-1 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 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 

Downstream Products

• 38344-08-0 (5Z)-bimatoprost acid 

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.

A Stable and Easily Prepared Catalyst for the Enantioselective Reduction of Ketones. Applications to Multistep Synthesis

-