Technology Process of ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate
There total 11 articles about ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate;
With
potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.5h;
Inert atmosphere;
With
2,4,6-Triisopropylbenzenesulfonyl azide;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.0833333h;
Inert atmosphere;
With
acetic acid;
In
tetrahydrofuran; toluene;
at -78 - 20 ℃;
for 0.5h;
Inert atmosphere;
DOI:10.1016/j.tet.2011.08.094
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 95 percent / imidazole / tetrahydrofuran / 16 h / 20 °C
2.1: 82 percent / POCl3 / pyridine / 0.75 h / 35 °C
3.1: 85 percent / Et3N; DMAP / CH2Cl2 / 16 h / 20 °C
4.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C
4.2: 62 percent / acetonitrile / 2 h / 20 °C
5.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C
5.2: 53 percent / tetrahydrofuran / -40 - 20 °C
6.1: 62 percent / KHMDS; trisyl azide; AcOH / tetrahydrofuran / -78 °C
With
1H-imidazole; dmap; 2,6-dichloro-benzonitrile; 2,4,6-Triisopropylbenzenesulfonyl azide; copper(I) thiophenolate; potassium hexamethylsilazane; acetic acid; triethylamine; lithium chloride; trichlorophosphate;
In
tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
4.2: Horner-Wadsworth-Emmons reaction / 5.2: Michael addition;
DOI:10.1039/b417625c
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 82 percent / POCl3 / pyridine / 0.75 h / 35 °C
2.1: 85 percent / Et3N; DMAP / CH2Cl2 / 16 h / 20 °C
3.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C
3.2: 62 percent / acetonitrile / 2 h / 20 °C
4.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C
4.2: 53 percent / tetrahydrofuran / -40 - 20 °C
5.1: 62 percent / KHMDS; trisyl azide; AcOH / tetrahydrofuran / -78 °C
With
dmap; 2,6-dichloro-benzonitrile; 2,4,6-Triisopropylbenzenesulfonyl azide; copper(I) thiophenolate; potassium hexamethylsilazane; acetic acid; triethylamine; lithium chloride; trichlorophosphate;
In
tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
3.2: Horner-Wadsworth-Emmons reaction / 4.2: Michael addition;
DOI:10.1039/b417625c