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

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

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 
• 104995-81-5 E-(S)-(+)-1-phenyloct-1-en-3-ol 
• 551-11-1 dinoprost 
• 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 
• 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 
• 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 

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

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.

TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. X. SYNTHESIS OF γ-KETO ESTERS AND THEIR REACTION WITH SOME ALUMINUM- AND BORON-CONTAINING REAGENTS

The cuprate synthesis of the monotetrahydrofuryl-γ-keto ester from 2-methoxycarbonyl-4-trimethylsilyloxy-2-cyclopenten-1-one and the active diastereomer (SS + RR) of 3-(2-tetrahydrofuryloxy)iodooctenol is described.The stereoselectivity of the reaction of the mono- and bistetrahydrofuryl-γ-keto esters with some aluminum- and boron-containing reagents was investigated, and the possibility of the production of the corresponding lactones with good yields was demonstrated.The reaction of the γ-keto esters and lactones with lithium selectride gave the corresponding γ-lactol, which together with the γ-lactones is the basic raw material for the synthesis of prostaglandins.

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

Stereocontrolled Synthesis of Prostaglandins from Cyclopentadiene Monoepoxide

Two complementary syntheses of prostaglandins from the same key intermediate 3, available in four steps from cyclopentadiene monoepoxide, are described.In one approach, a saturated α-chain is introduced via a 1,4-addition of an appropriately functionalized cyanocuprate reagent onto silyl enol ether 3.The resulting prostanoid compound was converted into the bronchodilator 1-decarboxy-1-hydroxymethyl PGE1, PGE1, and PGF1α.The second approach involves the transformation of silyl enol ether 3 into the known prostanoid precursor 11 via selective addition of carbethoxycarbene and subsequent fluoride-induced ring opening of the resulting (silyloxy)cyclopropane carboxylate ester.

Total Synthesis of (+/-)-Prostaglandin E2 Methyl Ester from exo-2-Bromo-endo-3-hydroxybicycloheptan-6-one using Dimethyl-t-butylsilyl Protected Intermediates

Peracetic acid oxidation at -78 deg C of the dihydroxybicyclohepten-6-one (23) afforded the dihydroxylactone (24) which was protected as its bisdimethyl-t-butylsilyl ether (26) and reduced to the corresponding lactol (27).A Wittig reaction on (27), carried out in benzene with a short reaction time, gave mainly the required 11α-silyl ether (28) together with a trace of the 9α-silyl ether (29) which results from 1,5-migration of the silyl group.Oxidation of (28) followed by quantitative deprotection using aqueous HF in acetonitrile afforded (+/-)-PGE2 methyl ester (20).This short stereo- and regioselective total synthesis proceeds in an overall yield of 10percent starting from cyclopentadiene.

Total Synthesis of Prostaglandin-F2α involving Stereocontrolled and Photo-induced Reactions of Bicycloheptanones

A short total synthesis of prostaglandin-F2α from cyclopentadiene is described.Acetalisation of bicyclohept-2-en-6-one (1) followed by formation of a singal bromohydrin gave on treatment with base the epoxyacetal (4).Reaction of (4) with the appropriate organocuprate reagent introduced both the 12β side-chain and 11α-hydroxy-group of the embryonic prostaglandin.The fused cyclobutane ring is important as it controls both the stereoselectivity of epoxide formation and the regioselectivity of the subsequent ring-opening reaction.Furthermore, the unusual photochemical behaviour of cyclobutanones was exploited in this synthesis.Irradiation of the bicycloheptan-6-one (9) in aqueous solution and subsequent Wittig olefination afforded prostaglandin-F2α.Baeyer-Villiger oxidation of the same ketone (9) furnished the lactone (16), a known precursor of prostaglandin-E.