Technology Process of methyl (E,3R,4R,5S)-N-benzyloxycarbonyl-α-(3,4-dibenzyloxy-5-benzyloxymethylpyrrolidine-2-ylidene)glycinate
There total 16 articles about methyl (E,3R,4R,5S)-N-benzyloxycarbonyl-α-(3,4-dibenzyloxy-5-benzyloxymethylpyrrolidine-2-ylidene)glycinate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 96 percent / NaBH4 / ethanol / 0.67 h / 0 °C
2: 74 percent / DMAP; Et3N / dimethylformamide / 24 h / 20 °C
3: 76 percent / imidazole / dimethylformamide / 48 h / 20 °C
4: 74 percent / p-TsOH / methanol; CH2Cl2 / 5 h / 20 °C
5: PDC / CH2Cl2 / 24 h / 20 °C
6: 62 percent / DBU / CH2Cl2 / 1.5 h / 20 °C
7: 73 percent / TBAF / tetrahydrofuran / 9 h / 20 °C
8: 2,6-lutidine / CH2Cl2 / 2 h / -40 - 0 °C
9: NaN3; benzyltrimethylammonium bromide / dimethylformamide; CH2Cl2 / 28 h / -40 - 0 °C
10: 61 percent / silica gel / 21 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; sodium azide; tetrabutyl ammonium fluoride; silica gel; trimethylbenzylammonium bromide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
1: Reduction / 2: Condensation / 3: Substitution / 4: Hydrolysis / 5: Oxidation / 6: Horner-Emmons reaction / 7: Substitution / 8: Substitution / 9: Substitution / 10: Cycloaddition;
DOI:10.1016/S0040-4020(99)00753-X
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 83 percent / DBU / CH2Cl2 / 0.5 h / 20 °C
2: 88 percent / HF*pyridine / tetrahydrofuran; pyridine / 22.5 h / 0 - 20 °C
3: 2,6-lutidine / CH2Cl2 / 2 h / -40 - 0 °C
4: NaN3; benzyltrimethylammonium bromide / dimethylformamide; CH2Cl2 / 28 h / -40 - 0 °C
5: 61 percent / silica gel / 21 h / 20 °C
With
2,6-dimethylpyridine; sodium azide; silica gel; trimethylbenzylammonium bromide; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;
1: Horner-Emmons reaction / 2: Substitution / 3: Substitution / 4: Substitution / 5: Cycloaddition;
DOI:10.1016/S0040-4020(99)00753-X
