Technology Process of tert-butyl (Z,4R,5R,6S)-6-azido-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-2-heptenoate
There total 10 articles about tert-butyl (Z,4R,5R,6S)-6-azido-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-2-heptenoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium azide; trimethylbenzylammonium bromide;
In
dichloromethane; N,N-dimethyl-formamide;
at -40 - 0 ℃;
for 28h;
DOI:10.1016/S0040-4020(99)00753-X
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: CH2Cl2 / 1 h / 20 °C
1.2: 2.45 g / BF3*Et2O / CH2Cl2 / 1 h / -20 °C
2.1: 95 percent / imidazole / dimethylformamide / 2 h / 20 °C
3.1: 1.98 g / Hg(ClO4)2*3H2O; CaCO3; H2O / tetrahydrofuran / 3 h / 20 °C
4.1: 54 percent / DBU / CH2Cl2 / 22 h / 20 °C
5.1: 23 percent / HF*pyridine / tetrahydrofuran; pyridine / 25 h / 0 °C
6.1: 2,6-lutidine / CH2Cl2 / 1.5 h / -40 - 0 °C
7.1: NaN3; benzyltrimethylammonium bromide / dimethylformamide; CH2Cl2 / 28 h / -40 - 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; sodium azide; mercury(II) perchlorate; water; trimethylbenzylammonium bromide; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium carbonate;
In
tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;
1.1: Substitution / 1.2: Rearrangement / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Horner-Emmons reaction / 5.1: Substitution / 6.1: Substitution / 7.1: Substitution;
DOI:10.1016/S0040-4020(99)00753-X
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 3.05 g / aq. NaOH / dioxane / 3.8 h / 20 °C
2: 2.26 g / DMAP / 2-methyl-propan-2-ol / 3 h / 20 °C
3: 54 percent / DBU / CH2Cl2 / 22 h / 20 °C
4: 23 percent / HF*pyridine / tetrahydrofuran; pyridine / 25 h / 0 °C
5: 2,6-lutidine / CH2Cl2 / 1.5 h / -40 - 0 °C
6: NaN3; benzyltrimethylammonium bromide / dimethylformamide; CH2Cl2 / 28 h / -40 - 0 °C
With
2,6-dimethylpyridine; dmap; sodium hydroxide; sodium azide; trimethylbenzylammonium bromide; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
1: Hydrolysis / 2: Etherification / 3: Horner-Emmons reaction / 4: Substitution / 5: Substitution / 6: Substitution;
DOI:10.1016/S0040-4020(99)00753-X
