Technology Process of (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester
There total 7 articles about (5Z)-(9S,11R,15R)-16-(3-chlorophenoxy)-9,11-dihydroxy-15-fluoro-17,18,19,20-tetranor-5-prostenoic acid isopropyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 97 percent / H2 / Pd/C / ethyl acetate / atmospheric pressure
2.1: 33 percent / (diethylamino)sulfur trifluoride / CH2Cl2
3.1: 67 percent / K3CO3 / methanol
4.1: 82 percent / p-TsOH*H2O / CH2Cl2
5.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C
6.1: potassium t-butoxide / tetrahydrofuran / 0.25 h
6.2: tetrahydrofuran
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C
8.1: 31 mg / HCl / H2O; propan-2-ol
With
hydrogenchloride; diethylamino-sulfur trifluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; isopropyl alcohol; acetone; toluene;
6.2: Wittig condensation;
DOI:10.1016/j.bmc.2004.04.034
- Guidance literature:
-
Multi-step reaction with 5 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
5.1: 31 mg / HCl / H2O; propan-2-ol
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
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 67 percent / K3CO3 / methanol
2.1: 82 percent / p-TsOH*H2O / CH2Cl2
3.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / -78 °C
4.1: potassium t-butoxide / tetrahydrofuran / 0.25 h
4.2: tetrahydrofuran
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 - 20 °C
6.1: 31 mg / HCl / H2O; propan-2-ol
With
hydrogenchloride; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; acetone; toluene;
4.2: Wittig condensation;
DOI:10.1016/j.bmc.2004.04.034
![[3aR,4R(1E,3S),5R,6aS]-5-benzoyloxy-4-[4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-one](/Databaselist/images/loading.webp)
