Technology Process of N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-16-methylheptadecan-2-yl)-2-methylpropane-2-sulfinamide
There total 6 articles about N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-16-methylheptadecan-2-yl)-2-methylpropane-2-sulfinamide 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
samarium diiodide;
In
tetrahydrofuran; tert-butyl alcohol;
at -78 ℃;
for 5h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1016/j.tet.2012.05.120
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran / 6 h / -78 - 20 °C
2.1: palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide / methanol / 12 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 3 h / -78 °C
4.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
4.2: 6 h / -78 - 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
6.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere
6.2: 4 h / 20 °C / Saturated solution
7.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere
With
n-butyllithium; samarium diiodide; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; toluene; tert-butyl alcohol;
1.1: Wittig reaction / 3.1: Swern oxidation / 4.1: Wittig reaction / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2012.05.120
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide / methanol / 12 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / 3 h / -78 °C
3.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
3.2: 6 h / -78 - 20 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C
5.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere
5.2: 4 h / 20 °C / Saturated solution
6.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere
With
n-butyllithium; samarium diiodide; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; toluene; tert-butyl alcohol;
2.1: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction;
DOI:10.1016/j.tet.2012.05.120
