Technology Process of (1R,2R,3aS,9aS)-2-((tert-butyldiphenylsilyl)oxy)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-ol
There total 13 articles about (1R,2R,3aS,9aS)-2-((tert-butyldiphenylsilyl)oxy)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
n-butyllithium; diphenylphosphane;
In
tetrahydrofuran; hexane;
for 19h;
Inert atmosphere;
Reflux;
- Guidance literature:
-
Multi-step reaction with 8 steps
1: hydrogen; 15 wt% palladium on carbon; potassium carbonate / tetrahydrofuran / 517.16 Torr
2: sodium tetrahydroborate; sodium hydroxide / ethanol; water / 18 h / -10 °C / Inert atmosphere
3: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 50 °C / Inert atmosphere
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
5: triethylamine; dmap / dichloromethane / 15 h / 0 °C / Inert atmosphere
6: potassium carbonate / methanol / 24 h / Inert atmosphere
7: copper(l) iodide / diethyl ether; hexane / 0.5 h / -78 - -40 °C / Inert atmosphere
8: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 19 h / Inert atmosphere; Reflux
With
1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; 15 wt% palladium on carbon; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; triethylamine; diphenylphosphane; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 7 steps
1: sodium tetrahydroborate; sodium hydroxide / ethanol; water / 18 h / -10 °C / Inert atmosphere
2: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 50 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
4: triethylamine; dmap / dichloromethane / 15 h / 0 °C / Inert atmosphere
5: potassium carbonate / methanol / 24 h / Inert atmosphere
6: copper(l) iodide / diethyl ether; hexane / 0.5 h / -78 - -40 °C / Inert atmosphere
7: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 19 h / Inert atmosphere; Reflux
With
1H-imidazole; dmap; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; diphenylphosphane; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;