Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS No.: 118908-17-1
• Molecular Formula: C₂₇H₂₈O₇
• Molecular Weight: 464.515
• Mol file: 118908-17-1.mol

Synonyms:Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property of Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

There total 3 articles about Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 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: 90.0%

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-5-methoxycarbonyl-3-oxo-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (118908-16-0) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (118908-17-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h; Ambient temperature;

DOI:10.1039/P19880002821

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (118908-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dicyclohexylcarbodi-imide; 2.) dichloroacetic acid; 3.) oxalic acid / 1.) benzene, DMSO, 5 min; 2.) 20 min, 3.) methanol, 10 min

2: tetrahydrofuran / 3 h / Ambient temperature

3: 90 percent / H₂ / palladium-carbon / ethyl acetate / 4 h / Ambient temperature

With dichloro-acetic acid; hydrogen; oxalic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1039/P19880002821

Reference yield:

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1) → Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (118908-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / Ambient temperature

2: 90 percent / H₂ / palladium-carbon / ethyl acetate / 4 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1039/P19880002821

upstream raw materials:

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-5-methoxycarbonyl-3-oxo-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

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

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

Downstream raw materials:

methyl 3-<2-(2-octan-t-6-yl>ethyl)-1,3-dithiolan-2-yl>propionate

(Z)-9α-11β-dihydroxy-15-oxo-2,3,18.19-tetranorprost-5-ene-1,20-dioic acid

6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid