[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

Base Information

• Chemical Name: [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
• CAS No.: 114488-91-4
• Molecular Formula: C31H27F3O6
• Molecular Weight: 552.547
• Mol file: 114488-91-4.mol

Synonyms:[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

Chemical Property of [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

Chemical Property:

• Melting Point: 130-133 °C
• Boiling Point: 706.5±60.0 °C(Predicted)
• PKA: 13.34±0.20(Predicted)
• PSA: 82.06000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 5.84550

Purity/Quality:

98% ^*data from raw 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-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester

There total 21 articles about [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 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: 73.51%

[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) → [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 (114488-91-4)

Guidance literature:

With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In dichloromethane; at -7 - 28 ℃; for 3h;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6aS)-4-[3R-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1E-butenyl]-5-(4-phenylbenzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one + [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 (114488-91-4)

Guidance literature:

Multi-step reaction with 6 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

6.1: D-Glucose; nicotinamide adenine dinucleotide phosphate / aq. phosphate buffer / pH 7 / Enzymatic reaction

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

DOI:10.1039/d1sc03237b

Reference yield:

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate (54094-19-8) → [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 (114488-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

2: lithium triethylborohydride / tetrahydrofuran / 0.5 h

With sodium hydride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1021/jm00143a018

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:

(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

(Z)-isopropyl 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-enoate

Refernces

• 1、 Chen, Fener,Huang, Zedu,Jiang, Meifen,Li, Weijian,Tang, Pei,Ye, Baijun,Zhang, Guo-Tai,Zhu, Kejie. "A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis". . p. 10362 - 10370. Retrieved 2021/08/16.
• 2、 -. "PROCESS FOR THE PREPARATION OF TRAVOPROST". . . Retrieved 2014/12/09.