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

• 78823-17-3 (1S*,4S*,1'E)-4-[{3'-(tert-butyldimethylsilyl)oxy}-1'-octenyl]-2-cyclopenten-1-ol 
• 78823-19-5 trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-cis-2,3-epoxycyclopentanol 
• 93566-61-1 1α,3α-2β-carbethoxy-5α-(methoxymethoxy)-4β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1β-<(triethylsilyl)oxy>bicyclo<3.1.0>hexane 
• 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 
• 93566-62-2 2α-(carbethoxymethyl)-3β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-4α-(methoxymethoxy)cyclopentanone 
• 93566-60-0 trans-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-4-(methoxymethoxy)-1-<(triethylsilyl)oxy>cyclopentene 
• 93566-56-4 trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene 
• 78823-20-8 trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone 
• 93566-63-3 3aα,6aα-4β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-5α-(methoxymethoxy)perhydropentafuran-2-one 
• 130891-76-8 (1SR,5RS,6RS,7RS)-7-hydroxy-6-(1-hydroxyoct-2-ynyl)-2-oxabicyclo<3.3.0>octan-3-one 
• 124287-12-3 (1SR,5RS,6RS,7RS)-7-acetoxy-6-<1-acetoxyoct-2(Z)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 
• 130891-80-4 (1SR,5RS,6RS,7RS)-7-hydroxy-6-<1-hydroxyoct-2(Z)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 
• 39178-67-1 (1E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene 

Downstream Products

• 363-24-6 dinoprostone 
• 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 
• 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 
• 104995-81-5 E-(S)-(+)-1-phenyloct-1-en-3-ol 
• 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.

Prostaglandins and Prostaglandin Intermediates. Part 26 A Novel Route to PGF2α using Triisopropoxy-hept-1-ynyl-titanium as Precursor for the β-Side Chain

The benzoylated Corey aldehyde 1a can be alkynylated with hept-1-ynyl-triisopropoxytitanium in good chemical yield and high diastereoselectivity to the (R)-alcohol 3c admixed with about 10percent of the diastereomeric (S)-alcohol 2c.Without removal of thi

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