[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]]

Base Information

• Chemical Name: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]]
• CAS No.: 54713-44-9
• Molecular Formula: C30H27ClO6
• Molecular Weight: 518.994
• Mol file: 54713-44-9.mol

Synonyms:[3aR-[3aalpha,4alpha(1E,3R^*),5beta,6aalpha]]-[1,1'-Biphenyl]-4-carboxylic acid 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester;

Chemical Property of [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]]

Chemical Property:

• Boiling Point: 726.3±60.0 °C(Predicted)
• PKA: 13.32±0.20(Predicted)
• PSA: 82.06000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 5.48010

Purity/Quality:

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

(3aR,4R,5R,6aS)-4-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-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:

• Uses: (3aR,4R,5R,6aS)-4-((R,E)-4-(3-Chlorophenoxy)-3-hydroxybut-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1''-biphenyl]-4-carboxylate is a reagent used in the synthesis of (+)-cloprostenol, a synthetic analogue of prostoglandin F2α.

Technology Process of [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]]

There total 35 articles about [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]] 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%

(3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate (54324-79-7) → (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 (54713-44-9)

Guidance literature:

With D-Glucose; nicotinamide adenine dinucleotide phosphate; In aq. phosphate buffer; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1039/d1sc03237b

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (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 (54713-44-9)

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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → 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 (54294-93-8,54713-44-9,54713-45-0,57378-78-6) + (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 (54713-44-9)

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; dimethyl sulfoxide / pH 7

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; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1039/d1sc03237b

upstream raw materials:

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

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

3-monochlorophenol

ethyl (3-chlorophenoxy)acetate

Downstream raw materials:

(+)-cloprostenol

(3aR,4R,5R,6aS)-4-((3R,E)-4-(3-chlorophenoxy)-3-(1-ethoxyethoxy)but-1-enyl)-5-(1-ethoxyethoxy)hexahydro-2Hcyclopenta[b]furan-2-ol

Refernces

• 1、 Chen, Yi,Yan, Hui,Chen, Hui-Xuan,Weng, Jiang,Lu, Gui. "An improved and efficient process for the preparation of (+)-cloprostenol". . p. 392 - 396. Retrieved 2015/06/02.