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

Uses

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

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 
• 67728-76-1 (1α,5α)-3β-hydroxy-2α-<(E)-(3R^*)-3-hydroxyoct-1-enyl>bicyclo<3.2.0>heptan-6-one 
• 78823-07-1 C₁₅H₂₉CuNOSi^(1-)*Li⁽¹⁺⁾ 
• 93566-61-1 (1R,3R,4R,5S)-4-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-3-methoxymethoxy-1-triethylsilanyloxy-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 

Downstream Products

• 363-24-6 dinoprostone 
• 104995-81-5 E-(S)-(+)-1-phenyloct-1-en-3-ol 
• 13345-50-1 prostaglandin A₂ 
• 38562-01-5 dinoprost tromethamine 
• 51388-75-1 (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol 
• 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 
• 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 
• 551-11-1 dinoprost 
• 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 
• 73070-15-2 (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate 

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.

SYNTHESIS OF (+/-)-PROSTAGLANDIN F2α

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