31752-99-5

Basic information

• Product Name: (-)-Corey lactone 4-phenylbenzoate alcohol
• Synonyms: (3AALPHA,4ALPHA,5BETA,6AALPHA)-(-)-HEXAHYDRO-4-(HYDROXYMETHYL)-2-OXO-2H-CYCLOPENTA[B]FURAN-5-YL 1,1'-BIPHENYL-4-CARBOXYLATE;(-)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL;(3aR,4S,5R,6aS)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one, 99%;(-)-COREY LACTONE 4-PHENYLBENZOATE;4-Phenylbenzoyl corey lactone;(-)-COREY LACTONE 4-PHENYLBENZOATE ALCOHOL 99%;[1,1'-Biphenyl]-4-carboxylicacid,(3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-ylester;BPCOD
• CAS NO: 31752-99-5
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.38
• EINECS: 1592732-453-0
• Product Categories: Prostaglandins;Latanoprost;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 31752-99-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131-132 °C(lit.)
• Boiling Point: 446°C (rough estimate)
• Flash Point: 210.6 °C
• Appearance: Off-white to pale yellow solid
• Density: 1.1818 (rough estimate)
• Vapor Pressure: 1.61E-14mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate
• PKA: 14.79±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 1294692
• CAS DataBase Reference: (-)-Corey lactone 4-phenylbenzoate alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Corey lactone 4-phenylbenzoate alcohol(31752-99-5)
• EPA Substance Registry System: (-)-Corey lactone 4-phenylbenzoate alcohol(31752-99-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 31752-99-5(Hazardous Substances Data)

Usage

Description

(-)-Corey lactone 4-phenylbenzoate alcohol is one of the isomers of biphenyl-4-formylcorilactone, which can be used for the synthesis of prostaglandins. Prostaglandins are a class of important endogenous physiologically active substances, important mediators of various physiological processes, and have high pharmacological activity. Clinically, prostaglandins are all artificially synthesized.

Chemical Properties

Off-White to Pale Yellow Solid

Uses

(-) Corey lactone phenylbenzoate is a key intermediate in the synthesis of prostaglandins. Versatile building block for prostaglandins. Building block for a potent and selective antiglaucoma agent analog of PGF2α.

InChI:InChI=1/C21H20O5/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/h1-9,16-19,22H,10-12H2

Upstream product

• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 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 
• 58707-50-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 165876-61-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 118560-20-6 <3aR(3aα,4α,5β,6aα)>-(-)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen pentanedioate 
• 118560-19-3 <3aR(3aα,4α,5β,6aα)>-(-)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate 
• 54382-73-9 <3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one 

Downstream Products

• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 165876-61-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 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 
• 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 
• 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 
• 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 
• 145667-74-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 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 
• 209861-01-8 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 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 
• 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 

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 short synthesis of optically active corey lactone by means of the dirhodium(II)-catalyzed intramolecular C-H insertion reaction of an α-diazo ketone

Optically active Corey lactone 8 has been synthesized using a dirhodium(II)-catalyzed intramolecular C-H insertion reaction of chiral α- diazo-β-oxo ester 2 as a key step.