Technology Process of ethyl (2E,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnon-2-enoate
There total 8 articles about ethyl (2E,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnon-2-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve
1.2: 12 h / -20 °C
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 °C
3.1: pyridine / dichloromethane / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C
4.2: 1 h / 20 °C
5.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / -78 °C
6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.75 h / -78 °C
7.1: benzene / 2 h / Reflux
With
pyridine; 1H-imidazole; titanium(IV) isopropylate; oxalyl dichloride; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; dichloromethane; toluene; benzene;
1.1: Sharpless asymmetric epoxidation / 1.2: Sharpless asymmetric epoxidation / 6.1: Swern oxidation / 7.1: Wittig reaction;
DOI:10.1055/s-0030-1260214
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 °C
2.1: pyridine / dichloromethane / 0 - 20 °C
3.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C
3.2: 1 h / 20 °C
4.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / -78 °C
5.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.75 h / -78 °C
6.1: benzene / 2 h / Reflux
With
pyridine; 1H-imidazole; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; dichloromethane; toluene; benzene;
5.1: Swern oxidation / 6.1: Wittig reaction;
DOI:10.1055/s-0030-1260214
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C
1.2: 1 h / 20 °C
2.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / -78 °C
3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.75 h / -78 °C
4.1: benzene / 2 h / Reflux
With
1H-imidazole; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; dichloromethane; benzene;
3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1055/s-0030-1260214