Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Base Information

• Chemical Name: Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS No.: 294856-04-5
• Molecular Formula: C₂₆H₂₅F₃O₅
• Molecular Weight: 474.477
• Mol file: 294856-04-5.mol

Synonyms:

Chemical Property of Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-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 Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

There total 5 articles about Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-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:

3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4) → Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (294856-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / 5 percent Pd/C / ethyl acetate

2.1: MeOH

3.1: N-BuLi / tetrahydrofuran / 0 °C

3.2: 80 percent / tetrahydrofuran

4.1: NaHMDS / 1,2-dimethoxy-ethane

4.2: 50 percent / 1,2-dimethoxy-ethane

5.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

With methanol; lithium aluminium tetrahydride; n-butyllithium; (-)-(S)-BINAL-H; hydrogen; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; 1.1: Catalytic hydrogenation / 2.1: Esterification / 3.1: Metallation / 3.2: Condensation / 4.1: Metallation / 4.2: Condensation / 5.1: Reduction;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

Benzoic acid (3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester (294856-03-4) → Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (294856-04-5)

Guidance literature:

With lithium aluminium tetrahydride; (-)-(S)-BINAL-H; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate (70783-99-2) → Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (294856-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHMDS / 1,2-dimethoxy-ethane

1.2: 50 percent / 1,2-dimethoxy-ethane

2.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

With lithium aluminium tetrahydride; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction;

DOI:10.1016/S0960-894X(00)00273-0

upstream raw materials:

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

3-(trifluoromethyl)cinnamic acid

dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

3-(3-trifluoromethylphenyl)propanoic acid

Downstream raw materials:

(3aR,4R,5R,6aS)-5-Hydroxy-4-[(E)-(S)-3-hydroxy-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-cyclopentyl}-hept-5-enoic acid

(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

17-(3-trifluoromethylphenyl)-17-trinor prostaglandin F_2α