39182-59-7

Usage

Uses

Used in Adhesives and Sealants:
Corey PG-lactone diol is used as a key component in the formulation of adhesives and sealants for its ability to enhance flexibility, low-temperature performance, and chemical resistance, resulting in improved adhesion and sealing properties.
Used in Coatings:
In the coatings industry, Corey PG-lactone diol is utilized as a critical ingredient to improve the flexibility and durability of the final product, ensuring a longer-lasting and more resilient coating.
Used in Elastomers:
Corey PG-lactone diol is employed as a vital constituent in the production of elastomers, where its unique properties contribute to the development of materials with superior flexibility and resistance to environmental factors.
Used as a Reactive Diluent in Polyurethane Dispersions and Other Polymers:
Corey PG-lactone diol is used as a reactive diluent in the formulation of polyurethane dispersions and other polymers, providing enhanced flexibility and durability to the final products, and improving their overall performance in various applications.

InChI:InChI=1/C15H24O4/c1-2-3-4-5-10(16)6-7-11-12-8-15(18)19-14(12)9-13(11)17/h6-7,10-14,16-17H,2-5,8-9H2,1H3/b7-6+

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 
• 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 
• 93566-67-7 trans-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-4-hydroxy-1-<(triethylsilyl)oxy>cyclopentene 
• 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 
• 130891-80-4 (1SR,5RS,6RS,7RS)-7-hydroxy-6-<1-hydroxyoct-2(Z)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 

Downstream Products

• 73089-64-2 (3'R)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate 
• 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 
• 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 

Relevant academic research and scientific papers

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.

Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of prostaglandins controlling the stereochemistry at C-15 using a silyl-to-hydroxy conversion following a stereochemically convergent synthesis of an allylsilane

Hydrosilylation of isoprene with chloro(diphenyl)silane gave (Z)-chloro(2-methylbut-2-enyl)-diphenylsilane 7. The cuprate reagent derived from this chloride underwent conjugate addition to methyl cinnamate 11, 1,2-silylcupration with hex-1-yne 16 and allene 18, and allylic displacement reactions with 1-vinylcyclohexyl acetate 20 and (Z)-1-cyclopentyloct-2-en-1-yl acetate 22. The silyl group in each of the products was converted into a hydroxy, with the removal of the 2-methylbut-2-enyl group taking place under much milder acidic conditions than those needed to remove the phenyl group from the dimethyl(phenyl)silyl group, and making this group suitable for the conversion of an allylsilane into an allyl alcohol. A stereospecifically anti conjugate displacement of the allylic benzoate group in (Z)-(1S,5R,6R,7R,1′S)-7-benzoyloxy-6-(1′-benzoyloxyoct-2′- enyl)-2-oxabicyclo[3.3.0]octan-3-one 52, and a stereospecifically syn conjugate displacement of the carbamate group in (Z)-(1S,5R,6R,7R,1′R)-7-benzoyloxy-6-(1′-N-phenylcarbamoyloxyoct- 2′-enyl)-2-oxabicyclo[3.3.0]octan-3-one 51, gave stereo-convergently the same allylsilane (1′ E,2″Z)-(1S,5S,6R,7R,3′S)-7-benzoyloxy-6-[3′-(2″- methylbut-2″-enyl)-diphenylsilyloct-1′-enyl]-2-oxabicyclo[3.3.0] octan-3-one 53. Silyl-to-hydroxy conversion gave the allyl alcohol (E)-(1S,5S,6R,7R,3′S)-7-benzoyloxy-6-(3′-hydroxyoct-1′-enyl)- 2-oxabicyclo[3.3.0]octan-3-one 54, having the relative and absolute stereochemistry at C-15 of the prostaglandins.

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.