(5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

Base Information

• Chemical Name: (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester
• CAS No.: 208112-11-2
• Molecular Formula: C₃₀H₄₅FO₆
• Molecular Weight: 520.682

Synonyms:(5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

Chemical Property of (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

There total 7 articles about (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl 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:

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate (51638-91-6) → (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester (208112-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 35 percent / (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / 1.5 h / 0 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate / 72 h / atmospheric pressure

3.1: (diethylamino)sulfur trifluoride / CH₂Cl₂

3.2: K₂CO₃ / ethanol

4.1: 140 mg / p-TsOH*H₂O / CH₂Cl₂

5.1: 92 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C

6.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

6.2: tetrahydrofuran

7.1: 50 mg / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C

With (+)-β-chlorodiisopinocampheylborane; diethylamino-sulfur trifluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; toluene; 6.2: Wittig condensation;

DOI:10.1016/j.bmc.2004.04.034

Reference yield:

[3aR,4R(1E,3S),5R,6aS]-5-benzoyloxy-4-(3-hydroxy-4-phenoxy-1-buten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one (51705-18-1) → (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester (208112-11-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate / 72 h / atmospheric pressure

2.1: (diethylamino)sulfur trifluoride / CH₂Cl₂

2.2: K₂CO₃ / ethanol

3.1: 140 mg / p-TsOH*H₂O / CH₂Cl₂

4.1: 92 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C

5.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

5.2: tetrahydrofuran

6.1: 50 mg / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C

With diethylamino-sulfur trifluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; toluene; 5.2: Wittig condensation;

DOI:10.1016/j.bmc.2004.04.034

Reference yield:

2-iodo-propane (75-30-9) + (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid → (5Z)-(9S,11R,15R)-9-hydroxy-15-fluoro-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester (208112-11-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

2-iodo-propane

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

[3aR,4R(3R),5R,6aS]-4-(3-fluoro-4-phenoxybutyl)-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

[3aR,4R(1E,3S),5R,6aS]-5-benzoyloxy-4-(3-hydroxy-4-phenoxy-1-buten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester

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