Technology Process of (S)-2-acetamido-N5-(3-(benzyloxy)-2-((benzyloxy)methyl)propyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide
There total 10 articles about (S)-2-acetamido-N5-(3-(benzyloxy)-2-((benzyloxy)methyl)propyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 5 steps
1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tetrahydrofuran; tert-butyl alcohol / 0.67 h
2: diphenyl phosphoryl azide; triethylamine / dichloromethane / 2 h / 0 - 20 °C
3: 34 h / Reflux
4: trifluoroacetic acid / dichloromethane / 10 h
5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling
With
sodium chlorite; 1-hydroxy-7-aza-benzotriazole; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jm500045x
- Guidance literature:
-
Multi-step reaction with 2 steps
1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 3 h
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling
With
1-hydroxy-7-aza-benzotriazole; palladium on activated charcoal; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jm500045x
- Guidance literature:
-
Multi-step reaction with 6 steps
1: acetic acid / water; tetrahydrofuran / 18 h
2: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tetrahydrofuran; tert-butyl alcohol / 0.67 h
3: diphenyl phosphoryl azide; triethylamine / dichloromethane / 2 h / 0 - 20 °C
4: 34 h / Reflux
5: trifluoroacetic acid / dichloromethane / 10 h
6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling
With
sodium chlorite; 1-hydroxy-7-aza-benzotriazole; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jm500045x