Technology Process of (1R,1R,2S,3S,4'S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol
There total 19 articles about (1R,1R,2S,3S,4'S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol 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:
-
With
n-butyllithium; zinc(II) chloride;
In
tetrahydrofuran; hexane;
at -78 - 0 ℃;
for 1.5h;
DOI:10.1016/S0040-4020(98)00484-0
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: 100 percent / diisopropylethylamine / CH2Cl2 / 10 h / 0 - 20 °C
2.1: 98 percent / LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C
3.1: 92 percent / CBr4; Ph3P / CH2Cl2 / 0.5 h / 0 °C
4.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C
5.1: 96 percent / H2 / Pd/C / ethanol / 20 h / 760 Torr
6.1: 88 percent / CBr4; Ph3P / CH2Cl2 / 0.5 h / 0 °C
7.1: 86 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C
8.1: 96 percent / HCl / methanol / 0.5 h / 60 °C
9.1: 85 percent / Et3N; DMAP / CH2Cl2 / 1 h / 0 °C
10.1: LAH / tetrahydrofuran / 1 h / 0 - 20 °C
10.2: 93 percent / imidazole / tetrahydrofuran / 10 h / 0 - 20 °C
11.1: 85 percent / formic acid / diethyl ether / 0.5 h / 0 °C
12.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -78 - 0 °C
13.1: n-BuLi; ZnCl2 / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane;
1.1: Etherification / 2.1: Reduction / 3.1: Bromination / 4.1: Addition / 5.1: Reduction / 6.1: Bromination / 7.1: Addition / 8.1: Elimination / 9.1: Etherification / 10.1: Reduction / 10.2: Etherification / 11.1: Elimination / 12.1: Swern oxidation / 13.1: Addition;
DOI:10.1016/S0040-4020(98)00484-0
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 98 percent / LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C
2.1: 92 percent / CBr4; Ph3P / CH2Cl2 / 0.5 h / 0 °C
3.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C
4.1: 96 percent / H2 / Pd/C / ethanol / 20 h / 760 Torr
5.1: 88 percent / CBr4; Ph3P / CH2Cl2 / 0.5 h / 0 °C
6.1: 86 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C
7.1: 96 percent / HCl / methanol / 0.5 h / 60 °C
8.1: 85 percent / Et3N; DMAP / CH2Cl2 / 1 h / 0 °C
9.1: LAH / tetrahydrofuran / 1 h / 0 - 20 °C
9.2: 93 percent / imidazole / tetrahydrofuran / 10 h / 0 - 20 °C
10.1: 85 percent / formic acid / diethyl ether / 0.5 h / 0 °C
11.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 2 h / -78 - 0 °C
12.1: n-BuLi; ZnCl2 / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane;
1.1: Reduction / 2.1: Bromination / 3.1: Addition / 4.1: Reduction / 5.1: Bromination / 6.1: Addition / 7.1: Elimination / 8.1: Etherification / 9.1: Reduction / 9.2: Etherification / 10.1: Elimination / 11.1: Swern oxidation / 12.1: Addition;
DOI:10.1016/S0040-4020(98)00484-0
