Technology Process of dimethyl (2S,4E,7S)-2,7-bis(benzyloxycarbonylamino)oct-4-en-1,8-dioate
There total 9 articles about dimethyl (2S,4E,7S)-2,7-bis(benzyloxycarbonylamino)oct-4-en-1,8-dioate which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
1,4-Bis((2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-(E)-but-2-ene;
With
hydrogenchloride;
In
tetrahydrofuran;
benzyl chloroformate;
With
N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran;
at 0 ℃;
Further stages.;
DOI:10.1021/ol0065423
- Guidance literature:
-
Multi-step reaction with 8 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
7.1: aq. HCl / tetrahydrofuran / 12.5 h
8.1: 808 mg / Et3N / tetrahydrofuran / 2.5 h / 20 °C
With
hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; borane; triethylamine; 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 / 7.1: Hydrolysis / 8.1: Acylation;
DOI:10.1021/ol0065423
- Guidance literature:
-
Multi-step reaction with 7 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
6.1: aq. HCl / tetrahydrofuran / 12.5 h
7.1: 808 mg / Et3N / tetrahydrofuran / 2.5 h / 20 °C
With
hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; triethylamine; 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 / 6.1: Hydrolysis / 7.1: Acylation;
DOI:10.1021/ol0065423
