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

Base Information

• Chemical Name: isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
• CAS No.: 733036-95-8
• Molecular Formula: C₂₅H₃₅FO₅
• Molecular Weight: 434.548

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate 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: 32.0%

(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) → isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate (733036-95-8) + (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 (733036-94-7)

Guidance literature:

With hydrogenchloride; In water; isopropyl alcohol; for 0.75h;

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) → isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate (733036-95-8)

Guidance literature:

Multi-step reaction with 7 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

7.1: 32 percent / HCl / H₂O; propan-2-ol / 0.75 h

With hydrogenchloride; (+)-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; water; isopropyl alcohol; 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) → isopropyl (Z)-7-((1R,2R,3R,5S)-2-((S,E)-3-fluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate (733036-95-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: 32 percent / HCl / H₂O; propan-2-ol / 0.75 h

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

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

(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

(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

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

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