(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

Base Information

Chemical Name:(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
CAS No.:733036-94-7
Molecular Formula:C₂₅H₃₅FO₅
Molecular Weight:434.548
Hs Code.:

Synonyms:(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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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 95%+ or 98%+ ^*data from raw suppliers

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Technology Process of (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

There total 7 articles about (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 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%

: 242464-10-4
(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

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

: 733036-94-7
(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

Guidance literature:: With hydrogenchloride; In water; isopropyl alcohol; for 0.75h;
DOI:10.1016/j.bmc.2004.04.034

Reference yield:

: 51638-91-6
(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

: 733036-94-7
(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

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: 14 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:

: 242464-05-7
[3aR,4R(1E,3RS),5R,6aS]-4-(3-fluoro-4-phenoxy-1-buten-1-yl)-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

: 733036-94-7
(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

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: 14 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