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

Base Information

Chemical Name:(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester
CAS No.:208111-95-9
Molecular Formula:C₃₀H₄₄ClFO₆
Molecular Weight:555.127
Hs Code.:

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

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

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

There total 7 articles about (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic 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-[(R)-4-(3-Chloro-phenoxy)-3-fluoro-butyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

: 208111-95-9
(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic 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

: 208111-95-9
(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / p-TsOH*H₂O / CH₂Cl₂

2.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C

3.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

3.2: tetrahydrofuran

4.1: 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:

: 208111-92-6
[3aR,4R(3R),5R,6aS]-4-[4-(3-chlorophenoxy)-3-fluorobutyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

: 208111-95-9
(5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-15-fluoro-9-hydroxy-11-(tetrahydropyran-2-yloxy)-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / p-TsOH*H₂O / CH₂Cl₂

2.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C

3.1: potassium t-butoxide / tetrahydrofuran / 0.25 h

3.2: tetrahydrofuran

4.1: 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