(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate
• CAS No.: 38754-71-1
• Molecular Formula: C21H18O5
• Molecular Weight: 350.371
• UNII: UFT9QT3Y94
• Nikkaji Number: J2.876.212G
• Mol file: 38754-71-1.mol

Synonyms:38754-71-1;(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate;[(3aR,4R,5R,6aS)-4-formyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate;[1,1'-Biphenyl]-4-carboxylic acid(3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-ylester;(-)-Corey lactone aldehyde P-phenyl benzoate;Corey Lactone Aldehyde;Corey Aldehyde, (-)-;UFT9QT3Y94;SCHEMBL1347430;AKOS015896640;AC-24758;-2-oxo-2H-cyclopenta[b]furan-5-yl ester;[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro;(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate;(3aR,4R,5R,6aS)-4-formylhexahydro-5-(p-phenylbenzoyloxy)-2H-cyclopenta[b]furan-2-one;(3abeta,6abeta)-4beta-Formyl-5alpha-(4-biphenylylcarbonyloxy)hexahydro-2H-cyclopenta[b]furan-2-one;[1,1'-Biphenyl]-4-carboxylic acid, (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester;[1,1'-Biphenyl]-4-carboxylic acid, 4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester, [3aR-(3a?,4?,5?,6a?)]-;2H-Cyclopenta[b]furan, [1,1'-biphenyl]-4-carboxylic acid deriv.;[1,1'-Biphenyl]-4-carboxylic acid, 4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-

Chemical Property of (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Boiling Point: 574.827 °C at 760 mmHg
• Flash Point: 253.713 °C
• PSA: 69.67000
• Density: 1.323 g/cm³
• LogP: 3.02950
• Solubility.: DCM, Ethyl Acetate
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 350.11542367
• Heavy Atom Count: 26
• Complexity: 545

Purity/Quality:

99% ^*data from raw suppliers

(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1''-biphenyl]-4-carboxylate ^*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=C(C=C3)C4=CC=CC=C4)C=O
• 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)C=O
• Uses: (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1''-biphenyl]-4-carboxylate is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.

Technology Process of (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

There total 13 articles about (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-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: 87.3%

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1)

Guidance literature:

With 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 0 ℃; for 1h; Reagent/catalyst; Temperature;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 70 °C / 12751.3 Torr

2.1: sodium methylate / methanol / 25 °C

2.2: 25 °C

3.1: C₂₁H₂₁NOSi; copper dichloride; N-ethyl-N,N-diisopropylamine / acetonitrile; dichloromethane / 14 h / -20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; carbonic acid dimethyl ester; trichloroisocyanuric acid / ethyl acetate

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sulfuric acid; sodium methylate; C₂₁H₂₁NOSi; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester; copper dichloride; In methanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1039/d1sc03237b

Reference yield:

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (5307-99-3) → (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: D-Glucose; nicotinamide adenine dinucleotide phosphate; oxygen / aq. phosphate buffer; 2-methoxy-ethanol / 760.05 Torr / pH 7.5 / Enzymatic reaction

2.1: acetic acid; zinc / tetrahydrofuran / 70 °C / 5250.53 Torr

3.1: sulfuric acid / 70 °C / 12751.3 Torr

4.1: sodium methylate / methanol / 25 °C

4.2: 25 °C

5.1: C₂₁H₂₁NOSi; copper dichloride; N-ethyl-N,N-diisopropylamine / acetonitrile; dichloromethane / 14 h / -20 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; carbonic acid dimethyl ester; trichloroisocyanuric acid / ethyl acetate

With D-Glucose; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sulfuric acid; oxygen; sodium methylate; nicotinamide adenine dinucleotide phosphate; C₂₁H₂₁NOSi; acetic acid; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester; copper dichloride; zinc; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; 2-methoxy-ethanol; ethyl acetate; acetonitrile;

DOI:10.1039/d1sc03237b

upstream raw materials:

(-)-Corey lactone 5-(4-phenylbenzoate)

(3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

[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

C₃₃H₃₀O₆

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

(3aR,4R,5R,6aS)-4-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl[1,1′-biphenyl]-4-carboxylate

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF A CHIRAL PROSTAGLANDIN ENOL INTERMEDIATE AND INTERMEDIATE COMPOUNDS USEFUL IN THE PROCESS". Page/Page column 30-31. . Retrieved 2021/06/26.
• 2、 -. "He fluorine front row element intermediate preparation method (by machine translation)". Paragraph 0043; 0044; 0045; 0046; 0047; 0048. . Retrieved 2018/05/16.