(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

Base Information

Chemical Name:(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester
CAS No.:733037-27-9
Molecular Formula:C₃₀H₄₂ClFO₆
Molecular Weight:553.111
Hs Code.:

(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

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Chemical Property of (5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

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Technology Process of (5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

There total 7 articles about (5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-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:

: 75-30-9
2-iodo-propane

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

: 733037-27-9
(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

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:

: 110-87-2
3,4-dihydro-2H-pyran

: 733037-27-9
(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / p-TsOH*H₂O / CH₂Cl₂

2.1: DIBAL-H / tetrahydrofuran; toluene / -78 °C

3.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

3.2: tetrahydrofuran

4.1: 744 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

Reference yield:

: 733037-25-7
[3aR,4R(1E,3RS),5R,6aS]-4-[4-(3-chlorophenoxy)-3-fluoro-1-buten-1-yl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

: 733037-27-9
(5Z,13E)-(9S,11R,15RS)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5,13-prostadienoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / p-TsOH*H₂O / CH₂Cl₂

2.1: DIBAL-H / tetrahydrofuran; toluene / -78 °C

3.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

3.2: tetrahydrofuran

4.1: 744 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