Technology Process of ((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyloxy)-3-((3S,1E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)cyclopentyl)methyl 4-methylbenzenesulfonate
There total 10 articles about ((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyloxy)-3-((3S,1E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)cyclopentyl)methyl 4-methylbenzenesulfonate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
5%-palladium/activated carbon; hydrogen; potassium hydroxide;
In
methanol;
for 5h;
- Guidance literature:
-
Multi-step reaction with 6 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
With
1H-imidazole; n-butyllithium; 5%-palladium/activated carbon; methyllithium; hydrogen; copper(l) cyanide; toluene-4-sulfonic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;
- Guidance literature:
-
Multi-step reaction with 6 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
With
1H-imidazole; n-butyllithium; 5%-palladium/activated carbon; methyllithium; hydrogen; copper(l) cyanide; toluene-4-sulfonic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;