4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

Base Information

• Chemical Name: 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate
• CAS No.: 54294-93-8
• Molecular Formula: C₃₀H₂₇ClO₆
• Molecular Weight: 518.994
• Mol file: 54294-93-8.mol

Synonyms:

Chemical Property of 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

There total 15 articles about 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate 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:

(-)-(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

Reference yield:

(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) → 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:

With lithium triethylborohydride; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jm00143a018

Reference yield:

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (5307-99-3) → 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 8 steps

1.1: D-Glucose; nicotinamide adenine dinucleotide phosphate; oxygen / aq. phosphate buffer; 2-methoxy-ethanol / 760.05 Torr / pH 7.5 / Enzymatic reaction

2.1: acetic acid; zinc / tetrahydrofuran / 70 °C / 5250.53 Torr

3.1: sulfuric acid / 70 °C / 12751.3 Torr

4.1: sodium methylate / methanol / 25 °C

4.2: 25 °C

5.1: C₂₁H₂₁NOSi; copper dichloride; N-ethyl-N,N-diisopropylamine / acetonitrile; dichloromethane / 14 h / -20 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; carbonic acid dimethyl ester; trichloroisocyanuric acid / ethyl acetate

7.1: sodium hydroxide / dichloromethane; water

8.1: 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; oxygen; sodium methylate; nicotinamide adenine dinucleotide phosphate; C₂₁H₂₁NOSi; acetic acid; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester; sodium hydroxide; copper dichloride; zinc; In tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; 2-methoxy-ethanol; 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

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.