26054-67-1

Basic information

• Product Name: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-
• Synonyms: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-;2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octenyl]-, (3aR,4R,5R,6aS)-;(3AR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one;DN-DI (Corey PG-Lactone Diol);(3AR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-on
• CAS NO: 26054-67-1
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.34866
• Mol File: 26054-67-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 430.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.199±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.30±0.40(Predicted)
• CAS DataBase Reference: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-(26054-67-1)
• EPA Substance Registry System: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-(26054-67-1)

Safety Data

• Hazardous Substances Data: 26054-67-1(Hazardous Substances Data)

Usage

Description

2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)is a complex organic compound characterized by its unique molecular structure. It is a key intermediate in the synthesis of biologically active molecules, specifically prostaglandins, which play crucial roles in various physiological processes.

Uses

Used in Pharmaceutical Industry:
2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)is used as an intermediate in the synthesis of Prostaglandin E2 (P838610) for its significant biological potency. Prostaglandin E2 is involved in numerous physiological functions, including inflammation, pain, and regulation of blood flow. Its synthesis is essential for the development of medications targeting these processes.
Used in Research and Development:
In addition to its pharmaceutical applications, 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)is also utilized in research and development settings. It serves as a valuable compound for studying the structure-activity relationships of prostaglandins and their analogs, which can lead to the discovery of novel therapeutic agents with improved efficacy and reduced side effects.

Upstream product

• 60623-67-8 (-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane 
• 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 
• 542-92-7 cyclopenta-1,3-diene 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 62961-72-2 Corey aldehyde 
• 120417-68-7 (1SR,5RS,6RS,7RS)-7-acetoxy-6-<3-acetoxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 
• 93566-63-3 3aα,6aα-4β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-5α-(methoxymethoxy)perhydropentafuran-2-one 
• 67728-76-1 (1α,5α)-3β-hydroxy-2α-<(E)-(3S^*)-3-hydroxyoct-1-enyl>bicyclo<3.2.0>heptan-6-one 
• 60623-67-8 γ-lactone of 2β-(3-oxo-trans-1-octenyl)-3α-hydroxy-5α-hydroxy-1α-cyclopentylacetic acid 
• 114951-80-3 lactone of 5α-hydroxy-3α-(2-tetrahydrofuryloxy)-2β-<3α-(2-tetrahydrofuryloxy)-trans-1-octenyl>cyclopentyl-1α-acetic acid 
• 98318-84-4 2α-methoxycarbonylmethyl-4α-(2-tetrahydrofuryloxy)-3β-<3α-2-tetrahydrofuryloxy)-trans-1-octenyl>-1-cyclopentanone 
• 78823-20-8 trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone 

Downstream Products

• 363-24-6 dinoprostone 
• 73070-15-2 (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate 
• 113517-83-2 (3aR,4R,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-6a-phenylsulfanyl-hexahydro-cyclopenta[b]pyrrol-2-one 
• 104995-81-5 E-(S)-(+)-1-phenyloct-1-en-3-ol 
• 551-11-1 dinoprost 
• 113517-91-2 (3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-prop-1-ynyl-hexahydro-cyclopenta[b]pyrrol-2-one 
• 113517-90-1 (3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-trimethylsilanylethynyl-hexahydro-cyclopenta[b]pyrrol-2-one 
• 51388-75-1 (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol 
• 38562-01-5 dinoprost tromethamine 
• 13345-50-1 prostaglandin A₂ 

Relevant articles and documents

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.

PROSTANOIDS. XXXII. SYNTHESIS OF (+)-PROSTAGLANDIN F2α

Natural prostaglandin F2α was obtained from cyclopentadiene monoxide.The key stages of the synthesis included the following: Optical resolution of (+/-)-trans-2-carboxymethylcyclopent-3-en-1-ol with the transformation of its (-)-enantiomer into (-)-cis-2-oxabicyclooct-6-en-3-one and then into (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclooctan-3-one; selective oxidation of the latter by the DMSO-(COCl)2 system; condensation of the intermediate (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclooctan-3-one with dimethyl 2-oxoheptylphosphonate under the conditions of phase-transfer catalysis with the production of (-)-7α-hydroxy-6β-(3-oxo-1E-octenyl)-cis-2-oxabicyclooctan-3-one; conversion of the latter into (+)-PGF2α by standard methods.

Regio- and Stereoselectivity of the Reaction between Cyanocuprates and Cyclopentene Epoxides. Application to the Total Synthesis of Prostaglandins

A systematic study of the reaction between cyclopentene epoxides and alkyl-, alkenyl-, and arylcyanocuprates is described.Alkylcyanocuprates react with complete regio- and stereoselectivity to provide trans-4-alkylcyclopent-2-enols in excellent yields.Vin