Technology Process of (2S,3R,4S,5R,E)-2,3,4,5-tetra(benzyloxy)-8-methyl-N-((S)-2-oxoazepan-3-yl)non-6-enamide
There total 8 articles about (2S,3R,4S,5R,E)-2,3,4,5-tetra(benzyloxy)-8-methyl-N-((S)-2-oxoazepan-3-yl)non-6-enamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 3 steps
1.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; dihydrogen peroxide / acetonitrile; water; tert-butyl alcohol / 3 h / 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
2.2: 12 h / 20 °C
3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux
With
sodium chlorite; Hoveyda-Grubbs catalyst second generation; sodium dihydrogen phosphate monohydrate; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tet.2012.11.004
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: triethylamine; dimethyl sulfoxide; oxalyl dichloride / dichloromethane / -78 °C
2.1: diisobutylaluminium hydride / diethyl ether / 0 °C
3.1: sodium hydride / tetrahydrofuran / 0.33 h / 20 °C
3.2: 12 h / 20 °C
4.1: acetonitrile / 12 h / Molecular sieve; Reflux
5.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
5.2: 0.17 h / 23 °C
6.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; dihydrogen peroxide / acetonitrile; water; tert-butyl alcohol / 3 h / 20 °C
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
7.2: 12 h / 20 °C
8.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux
With
sodium chlorite; sodium tetrahydroborate; Hoveyda-Grubbs catalyst second generation; sodium dihydrogen phosphate monohydrate; oxalyl dichloride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
1.1: |Swern Oxidation;
DOI:10.1016/j.tet.2012.11.004
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
1.2: 0.17 h / 23 °C
2.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; dihydrogen peroxide / acetonitrile; water; tert-butyl alcohol / 3 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
3.2: 12 h / 20 °C
4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux
With
sodium chlorite; sodium tetrahydroborate; Hoveyda-Grubbs catalyst second generation; sodium dihydrogen phosphate monohydrate; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tet.2012.11.004