(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde
• CAS No.: 39746-01-5
• Molecular Formula: C15H14O5
• Molecular Weight: 274.273
• Hs Code.: 2932209090
• European Community (EC) Number: 609-743-0
• DSSTox Substance ID: DTXSID80451415
• Nikkaji Number: J28.178F
• Wikidata: Q72461463
• Mol file: 39746-01-5.mol

Synonyms:39746-01-5;Corey aldehyde benzoate;Corey Lactone Aldehyde Benzoate;(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde;[(3aR,4R,5R,6aS)-4-formyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate;(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate;[3aR(3aalpha,4alpha,5beta,6aalpha)]-()-5-(Benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde;SCHEMBL1345364;DTXSID80451415;NDHMOBCVFGMXRK-FVCCEPFGSA-N;AKOS015896646;[3aR(3aalpha,4alpha,5beta,6aalpha)]-(-)-5-(Benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde;AC-24759;CS-0356872;(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]-octan-3-one;(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one;(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one;(1S,5R,6R,7R)-7-Benzoyloxy-3-oxo-2-oxabicyclo[3.3.0]octane-6-carbaldehyde;(3aR,4R,5R,6aS)-2-oxo-5-phenylcarbonyloxyhexahydro cyclopenta[b]furan-4-carbaldehyde;(3aR,4R,5R,6aS)-4-formyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate;(3ar,4r,5r,6as)-5-(benzoyloxy)hexahydro-2h-cyclopenta[b]furan-2-one-4-carboxaldehyde;3|A-Benzoyloxy-2|A-carboxaldehyde-5|A-hydroxy-1|A-cyclopentaneacetic Acid |A-Lactone;3beta-Benzoyloxy-2beta-carboxaldehyde-5alpha-hydroxy-1alpha-cyclopentaneacetic Acid gamma-Lactone

Chemical Property of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128-138 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 470.427 °C at 760 mmHg
• Flash Point: 211.802 °C
• PSA: 69.67000
• Density: 1.33 g/cm³
• LogP: 1.36250
• Storage Temp.: ?20°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 274.08412354
• Heavy Atom Count: 20
• Complexity: 413

Purity/Quality:

99% ^*data from raw suppliers

3β-Benzoyloxy-2β-carboxaldehyde-5α-hydroxy-1α-cyclopentaneaceticAcidγ-Lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=CC=C3)C=O
• Isomeric SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)C=O
• Description: Corey lactone aldehyde benzoate is a versatile, chiral intermediate used in the preparation of prostaglandins and prostaglandin analogs.
• Uses: (-)-Corey aldehyde benzoate is used in the synthesis of human FP-receptor selective prostaglandin analogues.

Technology Process of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde

There total 4 articles about (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde 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: 100.0%

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1039/a804276d

Reference yield:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde (51260-12-9) + (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5)

Guidance literature:

With sulfur trioxide pyridine complex; Inert atmosphere;

DOI:10.1021/jo901497u

Reference yield:

C15H16O5 (172821-93-1) → Benzoic acid (3aR,4R,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (39746-01-5,61348-03-6,61348-04-7,98673-94-0,118711-80-1)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In dichloromethane; at 0 ℃; for 0.5h;

upstream raw materials:

C₁₅H₁₆O₅

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Downstream raw materials:

C₂₂H₂₆O₅

(3aR,4R,5R,6aS)-5-(Benzoyloxy)4-[(E)-3-cyclohexyl-3-oxo-1-propenyl]-hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate