(5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

Base Information

• Chemical Name: (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester
• CAS No.: 242464-10-4
• Molecular Formula: C₃₀H₄₃FO₆
• Molecular Weight: 518.666

Synonyms:

Chemical Property of (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

There total 6 articles about (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic 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:

2-iodo-propane (75-30-9) + (Z)-7-[(1R,2R,3R,5S)-2-((E)-3-Fluoro-4-phenoxy-but-1-enyl)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid (242464-07-9) → (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester (242464-10-4)

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

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,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester (242464-10-4)

Guidance literature:

Multi-step reaction with 6 steps

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

2.1: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 5 h / cooling

2.2: K₂CO₃ / methanol / 1 h

3.1: 58 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h

4.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / 3 h / cooling

5.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

5.2: tetrahydrofuran / 2.5 h

6.1: 236 mg / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C

With (+)-β-chlorodiisopinocampheylborane; diethylamino-sulfur trifluoride; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetone; toluene; 5.2: Wittig condensation;

DOI:10.1016/j.bmc.2004.04.034

Reference yield:

[3aR,4R(1E,3RS),5R,6aS]-4-(3-fluoro-4-phenoxy-1-buten-1-yl)-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one (242464-05-7) → (5Z,13E)-(9S,11R,15RS)-15-fluoro-9-hydroxy-16-phenoxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester (242464-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 58 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h

2.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / 3 h / cooling

3.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

3.2: tetrahydrofuran / 2.5 h

4.1: 236 mg / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C

With potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetone; toluene; 3.2: Wittig condensation;

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

2-iodo-propane

(Z)-7-[(1R,2R,3R,5S)-2-((E)-3-Fluoro-4-phenoxy-but-1-enyl)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

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

Downstream raw materials:

isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate

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

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