Technology Process of (2Z,4S,5S,6E,8S,9S)-methyl 4-(benzyloxy)-5,8,9-tris((tert-butyldimethylsilyl)oxy)deca-2,6-dienoate
There total 4 articles about (2Z,4S,5S,6E,8S,9S)-methyl 4-(benzyloxy)-5,8,9-tris((tert-butyldimethylsilyl)oxy)deca-2,6-dienoate 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:
-
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate;
With
sodium hydride;
In
tetrahydrofuran;
at 0 ℃;
for 0.5h;
Inert atmosphere;
(2R,3S,6S,7S,E)-2-(benzyloxy)-3,6,7-tris((tert-butyldimethylsilyl)oxy)oct-4-enal;
In
tetrahydrofuran;
at -78 ℃;
for 2h;
stereoselective reaction;
Inert atmosphere;
DOI:10.1016/j.tet.2012.06.002
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1.17 h / -78 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / methanol / 4 h / Reflux; Inert atmosphere
3.1: 1H-imidazole; dmap / dichloromethane / 3 h / Reflux; Inert atmosphere
4.1: pyridinium p-toluenesulfonate / ethanol / 8 h / 20 °C / Inert atmosphere
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Reflux; Inert atmosphere
6.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
6.2: 2 h / -78 °C / Inert atmosphere
With
1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; pyridinium p-toluenesulfonate; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate;
6.2: Wittig reaction;
DOI:10.1016/j.tet.2012.06.002
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: pyridinium p-toluenesulfonate / methanol / 4 h / Reflux; Inert atmosphere
2.1: 1H-imidazole; dmap / dichloromethane / 3 h / Reflux; Inert atmosphere
3.1: pyridinium p-toluenesulfonate / ethanol / 8 h / 20 °C / Inert atmosphere
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Reflux; Inert atmosphere
5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 2 h / -78 °C / Inert atmosphere
With
1H-imidazole; dmap; pyridinium p-toluenesulfonate; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate;
5.2: Wittig reaction;
DOI:10.1016/j.tet.2012.06.002
