39265-57-1

Basic information

• Product Name: (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL
• Synonyms: (3aR,4S,5R,6aS)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1'-biphenyl-4-carboxylate;(+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL;(3aS,4R,5S,6aR)-(+)-Hexahydro-4-(hydroxymethyl)-5-(4-phenylbenzoyloxy)cyclopenta[b]-furan-2-one;(3aS,4R,5S,6aR)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzyloxy)cyclopenta[b]furan-2-one;(3aS,4R,5S,6aR)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1'-Biphenyl]-4-carboxylic Acid
• CAS NO: 39265-57-1
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.38
• Product Categories: Chiral Building Blocks;Lactones;Organic Building Blocks
• Mol File: 39265-57-1.mol

Chemical Properties

• Melting Point: 134-136 °C(lit.)
• Boiling Point: 584.8°C at 760 mmHg
• Flash Point: 210.6°C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 1.61E-14mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL(39265-57-1)
• EPA Substance Registry System: (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL(39265-57-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 39265-57-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL is used as a key intermediate for the synthesis of prostaglandins, which are essential in various physiological processes and have a wide range of applications in medicine. Prostaglandins are known to play a role in inflammation, pain, and other conditions, making them valuable in the development of therapeutic drugs.
As a key intermediate in the synthesis of prostaglandins, (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL is crucial for the development of medications that target these physiological processes. Its importance in the pharmaceutical industry lies in its ability to contribute to the creation of drugs that can alleviate pain, reduce inflammation, and address other related health issues.

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/t16-,17-,18+,19-/m1/s1

Upstream product

• 76704-05-7 <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 54382-73-9 <3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one 
• 136982-11-1 <3aS(3aα,4α,5β,6aα)>-(+)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen pentanedioate 
• 136982-10-0 <3aS(3aα,4α,5β,6aα)>-(+)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate 
• 127783-76-0 <3aS(2aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)-4-(butyryloxymethyl)hexahydro-2H-cyclopentafuran-2-one 

Downstream Products

• 64982-35-0 (3aS,4R,5S,6aR)-hexahydro-5-(biphenyl-4-formyloxy)-4-(tert-butyldimethylsilyloxy methyl)-2H-cyclopenta[b]furan-2-one 
• 197523-93-6 (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 76704-05-7 <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one 

Relevant articles and documents

RESOLUTION OF A RACEMIC COREY LACTONE via ENANTIOSELECTIVE ESTERIFICATION

The (-)-enantiomer of Corey lactone Ia has been separated from its (+)-enantiomer Ib via enantioselective esterification of the latter using glycerol tributyrate and a catalytic amount of lipase from Candida cylindracea (EC 3.1.1.3) in an aprotic solvent

PREPARATION OF OPTICALLY PURE ENANTIOMERS OF COREY LACTONE BY RESOLUTION OF THE RACEMATE

Racemic hydrogen butanedioates (IIa, IIb) and hydrogen pentanedioates (IIIa, IIIb), prepared by reaction of racemic Corey alcohol Ia, Ib with the corresponding acid anhydride, were resolved by optically active bases to give the optically pure diastereoisomeric salts from which the individual enantiomers of hydrogen butanedioate IIa and IIb and hydrogen pentanedioate IIIa and IIIb were liberated.Acid-catalyzed transesterification with methanol converted these optically pure enantiomers into the pure (-)-enantiomer Ia and (+)-enantiomer Ib of the Corey lactone.