Technology Process of methyl (5Z,8R,9E,11S,12S,14Z)-8-(tert-butyldimethylsilyl)oxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoate
There total 11 articles about methyl (5Z,8R,9E,11S,12S,14Z)-8-(tert-butyldimethylsilyl)oxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoate 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:
-
methyl (5Z,8R,9E,11S,12S,14Z)-8-(tert-butyldimethylsilyl)oxy-11-hydroxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoate;
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
methyl iodide;
In
tetrahydrofuran;
at -78 - 20 ℃;
DOI:10.1016/j.tet.2014.04.040
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
1.2: -78 - -40 °C
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 0 °C
3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 0 - 20 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 6 h / -78 °C
5.1: triethylamine; lithium bromide / tetrahydrofuran / 1.5 h / 20 °C
5.2: 20 °C
6.1: cerium(III) chloride heptahydrate / methanol / 0.08 h / 20 °C
6.2: 1 h / -78 °C
7.1: sodium hexamethyldisilazane; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 1 h / -78 °C
7.2: -78 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; lithium hydroxide monohydrate; cerium(III) chloride heptahydrate; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; dicyclohexyl-carbodiimide; lithium bromide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/j.tet.2014.04.040
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
1.2: -78 - -40 °C
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 0 °C
3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 0 - 20 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 6 h / -78 °C
5.1: triethylamine; lithium bromide / tetrahydrofuran / 1.5 h / 20 °C
5.2: 20 °C
6.1: cerium(III) chloride heptahydrate / methanol / 0.08 h / 20 °C
6.2: 1 h / -78 °C
7.1: sodium hexamethyldisilazane; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 1 h / -78 °C
7.2: -78 - 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; lithium hydroxide monohydrate; cerium(III) chloride heptahydrate; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; dicyclohexyl-carbodiimide; lithium bromide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/j.tet.2014.04.040
