Technology Process of (6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine
There total 18 articles about (6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine 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:
-
(6Z,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-[(2S)-3-iodo-2-methylpropylidene]-8-methyloctahydroindolizine;
With
tert.-butyl lithium;
In
diethyl ether;
at -110 ℃;
With
zinc(II) chloride;
In
tetrahydrofuran;
at -78 - 0 ℃;
benzyl (1S,2E)-1-ethyl-3-iodo-2-methyl-2-propenyl ether;
With
tetrakis(triphenylphosphine) palladium(0);
In
benzene;
DOI:10.1021/ja991918x
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 91 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
2.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / dimethylformamide / 7 h / 0 - 20 °C
3.1: 95 percent / triphenylphosphine; iodine; imidazole / CH2Cl2 / 8 h / 20 °C
4.1: t-BuLi / diethyl ether; pentane / 0.5 h / -110 °C
4.2: ZnCl2 / diethyl ether; pentane; tetrahydrofuran / 2 h / -110 - 20 °C
4.3: 60 percent / Pd(PPh3)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; triphenylphosphine;
In
diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo0200466
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 85 percent / triphenylphosphine; carbon tetrabromide / CH2Cl2 / 1 h / 20 °C
2.1: 91 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
3.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / dimethylformamide / 7 h / 0 - 20 °C
4.1: 95 percent / triphenylphosphine; iodine; imidazole / CH2Cl2 / 8 h / 20 °C
5.1: t-BuLi / diethyl ether; pentane / 0.5 h / -110 °C
5.2: ZnCl2 / diethyl ether; pentane; tetrahydrofuran / 2 h / -110 - 20 °C
5.3: 60 percent / Pd(PPh3)4 / diethyl ether; pentane; various solvent(s) / 3 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; carbon tetrabromide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; triphenylphosphine;
In
diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo0200466
