Technology Process of (2S,5R,2'E,5'S)-2-[5'-(benzyloxycarbonylamino)-5'-carbomethoxy-pent-2-ene]-2,5-dihydro-5-isopropyl-3,6-dimethyloxypyrazine
There total 6 articles about (2S,5R,2'E,5'S)-2-[5'-(benzyloxycarbonylamino)-5'-carbomethoxy-pent-2-ene]-2,5-dihydro-5-isopropyl-3,6-dimethyloxypyrazine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 0.166667h;
methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-bromohex-4-enoate;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 8h;
Further stages.;
DOI:10.1021/ol0065423
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 75 percent / BH3 / tetrahydrofuran / 5.5 h / -5 °C
2.1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO3 / toluene; H2O / 3 h / 0 °C
3.1: toluene / 4.5 h / 100 °C
4.1: 87 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
5.1: 72 percent / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C
6.2: 89 percent / tetrahydrofuran; hexane / 8 h / -78 °C
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; borane; triphenylphosphine; sodium bromide;
sodium hydrogencarbonate;
In
tetrahydrofuran; hexane; dichloromethane; water; toluene;
1.1: Reduction / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Substitution;
DOI:10.1021/ol0065423
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO3 / toluene; H2O / 3 h / 0 °C
2.1: toluene / 4.5 h / 100 °C
3.1: 87 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
4.1: 72 percent / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C
5.2: 89 percent / tetrahydrofuran; hexane / 8 h / -78 °C
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; triphenylphosphine; sodium bromide;
sodium hydrogencarbonate;
In
tetrahydrofuran; hexane; dichloromethane; water; toluene;
1.1: Oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Substitution / 5.1: Metallation / 5.2: Substitution;
DOI:10.1021/ol0065423
