39746-00-4

Basic information

• Product Name: (-)-Corey Lactone Benzoate
• Synonyms: 5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one(3aα,4α,5β,6aα);(-)-5-(BENZOYLOXY)HEXAHYDRO-4-(HYDROXYME)-2H-CYCLOPENTA(B)FURAN-2-ONE, 97%;5-(BENZOYLOXY) HEXAHYDRO-4-(HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE;BENZOYL COREY LACTONE;(-)-COREY LACTONE BENZOATE 99%;(-)-COREY LACTONE BENZOATE: (3AR,4S,5R,6AS)-(-)-5-(BENZOYLOXY)-HEXAHYDRO-4(-HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE;(-)-6-BETA-HYDROXYMETHYL-7-ALPHA-BENZOYLOXY-CIS-2-OXABICYCLO[3.3.0]OCTAN-3-ONE(COREY''S LACTONE);(1R)-2β-(Hydroxymethyl)-3α-(benzoyloxy)-5α-hydroxycyclopentane-1α-acetic acid 1,5-lactone
• CAS NO: 39746-00-4
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28
• EINECS: 254-615-6
• Product Categories: Prostaglandins;Latanoprost
• Mol File: 39746-00-4.mol

Chemical Properties

• Melting Point: 116-120 °C
• Boiling Point: 379.19°C (rough estimate)
• Flash Point: 183.3oC
• Appearance: Colorless crystalline powder
• Density: 1.2379 (rough estimate)
• Vapor Pressure: 4.24E-10mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.79±0.10(Predicted)
• CAS DataBase Reference: (-)-Corey Lactone Benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Corey Lactone Benzoate(39746-00-4)
• EPA Substance Registry System: (-)-Corey Lactone Benzoate(39746-00-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 39746-00-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Corey lactone benzoate is used as a key intermediate in the synthesis of prostaglandin analogues for their application as vasodilators. These analogues help in relaxing blood vessels, which can be beneficial in treating conditions like hypertension and other cardiovascular diseases.
Additionally, (-)-Corey lactone benzoate is used in the preparation of EP4 receptor agonists. EP4 receptor agonists have potential therapeutic applications in various areas, including inflammation, pain management, and certain types of cancer.

InChI:InChI=1/C15H16O5/c16-8-11-10-6-14(17)19-12(10)7-13(11)20-15(18)9-4-2-1-3-5-9/h1-5,10-13,16H,6-8H2

Upstream product

• 65-85-0 benzoic acid 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 58707-50-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 101208-17-7 (3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one 
• 39746-01-5 (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 

Downstream Products

• 131543-59-4 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(bromomethyl)-2H-cyclopentafuran-2-one 
• 101208-17-7 (3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one 
• 912445-64-8 (3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydrocyclopenta(b)furan-2-one 
• 39968-95-1 (3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 551-11-1 dinoprost 
• 62939-85-9 (-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 618387-07-8 (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one 
• 131543-60-7 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one 
• 131543-63-0 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(4-hydroxy-2(E)-butenyl)-2H-cyclopentafuran-2-one 
• 131543-62-9 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(4-(tert-butyldimethylsiloxy)-2(E)-butenyl)-2H-cyclopentafuran-2-one 
• 131543-65-2 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R,3R)-2,3-epoxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one 
• 51638-92-7 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one 
• 131543-66-3 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylthio)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one 
• 131543-61-8 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2S)-2-hydroxy-(3S)-3-(phenylthio)-4-phenoxybutyl)-2H-cyclopentafuran-2-one 

Relevant articles and documents

One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization

A novel technique for the absolute stereochemical determination of alcohols has been developed that uses crystallization of guanidinium salts of organosulfates. The simple one-pot, two-step process leverages facile formation of guandinium organosulfate single crystals for the straightforward determination of the absolute stereochemistry of enantiopure alcohols by means of X-ray crystallography. The strong hydrogen bonding network drives the stability of the crystal lattice and allows for a diverse range of organic alcohol substrates to be analyzed.

Preparing method for benzoyl corey lactone

The invention provides a method for preparing a high-purity compound shown in a formula 3. The preparing method includes the steps that in dichloromethane, in the presence of diisopropylethylamine, primary alcohol of (-)-corey lactone shown in a formula 4 is protected with triethylchloro-silicane to obtain the compound shown in the formula 3; in the formula, R is the triethylchloro-silicane, wherein the molar ratio of the (-)-corey lactone shown in the formula 4 to the triethylchloro-silicane is 1-1.5, the molar ratio of the (-)-corey lactone shown in the formula 4 to the diisopropylethylamineis 1.5-3, and the mass/the volume (g/ml) of the (-)-corey lactone shown in the formula 4 to the dichloromethane is 3-10; the reaction temperature is 20 DEG C to 30 DEG C. The invention also providesa method for preparing benzoyl corey lactone shown in the formula 1 with the obtained high-purity compound shown in the formula 3. The method is good in selectivity, convenient to use and easy to industrialize, and therefore the (-)-corey lactone can be prepared at high yield. The formula is defined in the description.

One-pot method of preparing benzoyl the branch stands lactone (by machine translation)

The present invention discloses a one-pot method for preparing benzoyl the branch stands lactone. At the same in the reaction container, to the branch stands lactone diol as raw materials, adding solvent S1 And triphenyl methyl chloride to primary hydroxyl position of the alkylation reaction, to obtain [...] lactone solvent S [...] hydroxy derivatives1 The reaction system, benzoyl chloride to continue adding hydroxyl position of acylation reaction, and adding solvent S2 , Recrystallization, get the branch stands lactone glycol double-hydroxy derivative; adding solvent S3 And acid solution hydrolysis reaction of the primary hydroxyl group position, make the branch stands lactone crude benzoyl; adding solvent S4 Or/and S5 , Recrystallization, disposable and preparing the corresponding optically active benzoyl the branch stands lactone. The invention avoid each step reaction is repeatedly re-feeding the tedious; adequate reaction, little side reaction, high purity; after treatment is simple, high yield; and the operation is simple, time saving and high efficiency, saving the material, reducing the cost, and is suitable for industrial production. (by machine translation)

Transformation of δ-lactone in γ-lactone in the Corey route for synthesis of prostaglandins

(Un)substituted benzoate ester protected δ-lactone alcohols are alcoholized in acid catalysis in almost quantitative yield to hydroxyl-halogenoesters. For alkylesters the yield drops to ～70%. After changing the protection between primary and secondary alcohols, the intermediate halogenoesters are transformed into the known γ-lactone alcohols protected as ether, silyl-ether or trityl at the secondary alcohol group. Unprotected δ-lactone alcohol 1 is also quantitatively transformed in chloroester 20. After selective protection of the primary alcohol with bulky ether groups, this is finally transformed into the known Corey γ-lactone alcohol, protected as ester at the secondary alcohol.

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AL-8810: A novel prostaglandin F(2α) analog with selective antagonist effects at the prostaglandin F(2α) (FP) receptor

A novel analog of prostaglandin F(2α) [AL-8810; (5Z, 13E)-(9S,11S,15R)- 9,15-dihydroxy-11-fluoro-15-(2-indanyl)-16,17, 18,19,20-pentanor-5,13- prostadienoic acid] has been discovered with uniquely low efficacy (E(max)) at the endogenous prostaglandin F(2α) receptors (FP receptors) of A7r5 rat thoracic aorta smooth muscle cells and Swiss mouse 3T3 fibroblasts, as assayed by stimulation of phospholipase C activity. AL-8810 has weak agonist potency (EC50) of 261 ± 44 nM (n = 3) and E(max) = 19% (relative to the full FP receptor agonist cloprostenol) in A7r5 cells and EC50 of 186 ± 63 nM (n = 3) and E(max) = 23% in 3T3 fibroblasts. AL-8810 exhibited properties of an apparent competitive antagonist, i.e., produced parallel dextral shifts of the agonist concentration-response curves and no significant suppression of the maximal agonist-induced response, when the potent, selective FP receptor agonist fluprostenol was used. The inhibition parameters of AL-8810 were: pA2 = 6.68 ± 0.23 and 6.34 ± 0.09 (n = 3-4) for A7r5 cells and 3T3 cells, respectively, with Schild slopes ranging from 0.80 to 0.92. AL-8810 concentration-dependently antagonized the response to 100 nM fluprostenol (K(i) = 426 ± 63 nM; n = 5) in A7r5 cells. However, even at 10 μM concentration, AL-8810 did not significantly inhibit functional responses of TP, DP, EP2, EP4, receptor subtypes in various cell lines. AL-8810 also did not antagonize the phospholipase C-coupled V1-vasopressin receptor in A7r5 cells. These results suggest that AL-8810 is a unique, selective antagonist at the FP receptor, a heretofore unavailable pharmacological tool that should be valuable for studying FP receptor-mediated functional responses in complex biological systems.