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

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester
• CAS No.: 208112-15-6
• Molecular Formula: C₂₅H₃₇FO₅
• Molecular Weight: 436.564

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic 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: 67.0%

(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) → (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester (208112-15-6)

Guidance literature:

With hydrogenchloride; In water; isopropyl alcohol;

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) → (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester (208112-15-6)

Guidance literature:

Multi-step reaction with 8 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

8.1: 67 percent / HCl / H₂O; propan-2-ol

With hydrogenchloride; (+)-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; water; ethyl acetate; isopropyl alcohol; 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) → (Z)-7-[(1R,2R,3R,5S)-2-((R)-3-Fluoro-4-phenoxy-butyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester (208112-15-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: 67 percent / HCl / H₂O; propan-2-ol

With hydrogenchloride; 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; water; ethyl acetate; isopropyl alcohol; acetone; toluene; 5.2: Wittig condensation;

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

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

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