(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate
• CAS No.: 31752-99-5
• Molecular Formula: C21H20O5
• Molecular Weight: 352.387
• Hs Code.: 29322090
• European Community (EC) Number: 608-667-5
• UNII: 5Z6XHA7HUG
• DSSTox Substance ID: DTXSID00369124
• Nikkaji Number: J232.150E
• Wikipedia: Corey_lactone_4-phenylbenzoate
• Wikidata: Q5170469
• Mol file: 31752-99-5.mol

Synonyms:31752-99-5;(-)-Corey lactone 4-phenylbenzoate alcohol;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate;Corey lactone 4-phenylbenzoate;(-)-Corey Lactone 5-(4-Phenylbenzoate);[(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate;(-)-Corey lactone 4-phenylbenzoate;Corey lactone p-phenylbenzoate alcohol;(-)-Corey lactone,4-phenylbenzoate alcohol;(3aR,4S,5R,6aS)-[1,1'-Biphenyl]-4-carboxylic acid, hexahydro-4-(methoxymethyl)-2-oxo-2H-cyclopentafuran-5-yl ester;(-)-Corey lactone, 4-PBP;MFCD00078077;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate;Corey lactone, (-)-;5Z6XHA7HUG;TimTec1_004986;SCHEMBL12013754;DTXSID00369124;SZJVIFMPKWMGSX-AKHDSKFASA-N;HMS1548C14;AMY25117;AKOS024438682;AC-6092;CS-11497;C2756;CS-0003840;F20541;A820979;(-)-Corey lactone, 4-phenylbenzoate alcohol, 99%;Q5170469;2H-Cyclopenta[b]furan, [1,1'-biphenyl]-4-carboxylic acid deriv.;BIPHENYL-4-CARBOXYLIC ACID 4-HO-METHYL-2-OXO-6H-CYCLOPENTA(B)FURAN-5-YL ESTER;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl 4-Phenylbenzoate;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-ylBiphenyl-4-carboxylate;(3aR,4S,5R,6aS)-Hexahydro-4-(hydroxymethyl)-5-(4-phenylbenzoyloxy)-2H-cyclopenta[b]furan-2-one;[1,1'-Biphenyl]-4-carboxylic acid, hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl ester, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-;4-Biphenylcarboxylic acid, 5-ester with 3,3aalpha,4,5,6,6aalpha-hexahydro-5beta-hydroxy-4alpha-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one, (-)-

Chemical Property of (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

Chemical Property:

• Appearance/Colour: Off-white to pale yellow solid
• Vapor Pressure: 1.61E-14mmHg at 25°C
• Melting Point: 128-134 °C
• Refractive Index: 1.628
• Boiling Point: 584.8 °C at 760 mmHg
• PKA: 14.79±0.10(Predicted)
• Flash Point: 210.6 °C
• PSA: 72.83000
• Density: 1.32 g/cm³
• LogP: 2.82290
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: insoluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 352.13107373
• Heavy Atom Count: 26
• Complexity: 519

Purity/Quality:

99%min ^*data from raw suppliers

(-)-Corey Lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO
• Isomeric SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO
• Description: (-)-Corey lactone 4-phenylbenzoate alcohol is one of the isomers of biphenyl-4-formylcorilactone, which can be used for the synthesis of prostaglandins. Prostaglandins are a class of important endogenous physiologically active substances, important mediators of various physiological processes, and have high pharmacological activity. Clinically, prostaglandins are all artificially synthesized.
• Uses: (-) Corey lactone phenylbenzoate is a key intermediate in the synthesis of prostaglandins. Versatile building block for prostaglandins. Building block for a potent and selective antiglaucoma agent analog of PGF2α.

Technology Process of (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

There total 15 articles about (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.45%

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → (-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5)

Guidance literature:

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one; With pyridine; trityl chloride; at 20 ℃; for 12h; Large scale;

4-biphenyl-carboxylic acid chloride; at 30 ℃; for 4.5h; Temperature; Large scale;

Reference yield: 93.0%

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (165876-61-9) → (-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5)

Guidance literature:

With aluminium(III) chloride hexahydrate; In methanol; at 60 ℃; for 12h;

DOI:10.1016/j.bioorg.2016.09.003

Reference yield: 84.0%

<3aR(3aα,4α,5β,6aα)>-(-)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate (118560-19-3) → (-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5)

Guidance literature:

With sulfuric acid; In methanol; for 14h; Heating;

upstream raw materials:

<3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one

<3aR(3aα,4α,5β,6aα)>-(-)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate

<3aR(3aα,4α,5β,6aα)>-(-)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen pentanedioate

4-biphenyl-carboxylic acid chloride

Downstream raw materials:

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aα,4α,5β,6aα)-(-)-hexahydro-4-(methoxymethyl)-5-<(4-phenylphenyl)carboxy>-2H-cyclopentafuran-2-one

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-4-(3-chloro-phenoxy)-3-hydroxy-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Refernces

• 1、 González-Calderón, Davir,Mejía-Dionicio, María G.,Morales-Reza, Marco A.,Aguirre-de Paz, José G.,Ramírez-Villalva, Alejandra,Morales-Rodríguez, Macario,Fuentes-Benítes, Aydeé,González-Romero, Carlos. "Antifungal activity of 1′-homo-N-1,2,3-triazol-bicyclic carbonucleosides: A novel type of compound afforded by azide-enolate (3+2) cycloaddition". . p. 1 - 6. Retrieved 2016/09/23.