Technology Process of (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S,1E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate
There total 16 articles about (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S,1E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate 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:
- Guidance literature:
-
With
acetic acid;
In
tetrahydrofuran; water;
at 20 ℃;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-butyllithium; copper(l) cyanide; methyllithium / diethyl ether; hexane; tetrahydrofuran / 0.5 h / -70 °C
1.2: 0.5 h / -70 °C
2.1: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / Cooling with ice
2.2: 1 h / 20 °C
3.1: 1H-imidazole / ethyl acetate / 20 °C
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / Inert atmosphere
4.2: 1.75 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
6.1: hydrogen; potassium hydroxide; 5%-palladium/activated carbon / methanol / 5 h
7.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / Inert atmosphere; Reflux
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C
8.2: 0.5 h
9.1: acetic acid / tetrahydrofuran; water / 20 °C
With
1H-imidazole; n-butyllithium; 5%-palladium/activated carbon; methyllithium; hydrogen; copper(l) cyanide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; mineral oil;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-butyllithium; copper(l) cyanide; methyllithium / diethyl ether; hexane; tetrahydrofuran / 0.5 h / -70 °C
1.2: 0.5 h / -70 °C
2.1: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / Cooling with ice
2.2: 1 h / 20 °C
3.1: 1H-imidazole / ethyl acetate / 20 °C
4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / Inert atmosphere
4.2: 1.75 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
6.1: hydrogen; potassium hydroxide; 5%-palladium/activated carbon / methanol / 5 h
7.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / Inert atmosphere; Reflux
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C
8.2: 0.5 h
9.1: acetic acid / tetrahydrofuran; water / 20 °C
With
1H-imidazole; n-butyllithium; 5%-palladium/activated carbon; methyllithium; hydrogen; copper(l) cyanide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; mineral oil;