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

Base Information

• Chemical Name: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester
• CAS No.: 54142-64-2
• Molecular Formula: C31H25 F3 O6
• Molecular Weight: 550.531
• Mol file: 54142-64-2.mol

Synonyms:[1,1'-Biphenyl]-4-carboxylicacid,(3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-2H-cyclopenta[b]furan-5-ylester (9CI); [1,1'-Biphenyl]-4-carboxylic acid,hexahydro-2-oxo-4-[3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]-2H-cyclopenta[b]furan-5-ylester, [3aR-[3aa,4a(E),5b,6aa]]-; 2H-Cyclopenta[b]furan, [1,1'-biphenyl]-4-carboxylic acid deriv.

Chemical Property of [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128-129oC
• PSA: 78.90000
• Density: 1.37
• LogP: 6.05370

Purity/Quality:

98%,99%, ^*data from raw suppliers

[1,1'-BIPHENYL]-4-CARBOXYLIC ACID (3AR,4R,5R,6AS)-HEXAHYDRO-2-OXO-4-[(1E)-3-OXO-4-[3-(TRIFLUOROMETHYL)PHENOXY]-1-BUTEN-1-YL]-2H-CYCLOPENTA[B]FURAN-5-YL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester

There total 13 articles about [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-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: 91.0%

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate (54094-19-8) + (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1) → [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester (54142-64-2,40695-33-8,122921-57-7)

Guidance literature:

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate; With potassium carbonate; In isopropyl alcohol; at 25 ℃; for 0.5h;

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate; In isopropyl alcohol; at 25 ℃; for 3h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 55.0%

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) + dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate (54094-19-8) → [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester (54142-64-2,40695-33-8,122921-57-7)

Guidance literature:

(-)-Corey lactone 5-(4-phenylbenzoate); With phosphoric acid; diisopropyl-carbodiimide; In dimethyl sulfoxide; toluene; at 50 ℃; Inert atmosphere;

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate; With potassium hydroxide; In toluene; at -10 ℃;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester (54142-64-2,40695-33-8,122921-57-7)

Guidance literature:

Multi-step reaction with 5 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

5.1: sodium hydroxide / dichloromethane; water

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; sodium hydroxide; copper dichloride; In methanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1039/d1sc03237b

upstream raw materials:

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate

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

3-Trifluoromethylphenol

methyl 2-[3-(trifluoromethyl)phenoxy]acetate

Downstream raw materials:

[1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester

(3aR,4R,5R,6aS)-5-((2-methoxyethoxy)methoxy)-4-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-((2-methoxyethoxy)methoxy)-4-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-ol

(Z)-7-((1R,2R,3R,5S)-5-hydroxy-3-((2-methoxyethoxy)methoxy)-2-((R,E)-3-((2-methoxyethoxy)methoxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoic acid

Refernces

• 1、 -. "Novel method for preparing Prostaglandin derivatives". Paragraph 0136; 0150-0152. . Retrieved 2017/10/31.
• 2、 -. "PROCESS FOR THE PREPARATION OF TRAVOPROST". Paragraph 0034-0040. . Retrieved 2014/12/09.