Technology Process of (2R,6R,10R,14E)-1,16-bis-(tert-butyldimethylsilyloxy)-12-phenylsulfonyl-2,6,10,14-tetramethyl-14-hexadecen-6-ol
There total 16 articles about (2R,6R,10R,14E)-1,16-bis-(tert-butyldimethylsilyloxy)-12-phenylsulfonyl-2,6,10,14-tetramethyl-14-hexadecen-6-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:
-
(2R,6R,10R)-1-tert-butyldimethylsilyloxy-12-phenylsulfonyl-2,6,10-trimethyldodecan-6-ol;
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 0.5h;
Inert atmosphere;
(4-Bromo-3-methylbut-2-enyloxy)-tert-butyldimethylsilane;
In
tetrahydrofuran; hexane;
at -78 - 0 ℃;
DOI:10.1016/j.tet.2011.09.066
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: disodium hydrogenphosphate; sodium-mercury amalgam (5%) / tetrahydrofuran; methanol / 1.5 h / -15 - 20 °C
2.1: AD-mix-α; methanesulfonamide / water; tert-butyl alcohol / 0 °C
3.1: triethylamine / dichloromethane / 0 °C
4.1: potassium carbonate / methanol / 20 °C
5.1: lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6.1: ammonia; lithium / -40 °C
7.1: pyridine / 0 °C
8.1: sodium iodide / acetone / 20 °C / Reflux
9.1: N,N-dimethyl-formamide / 6 h
10.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
10.2: -78 - 0 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium-mercury amalgam (5%); n-butyllithium; methanesulfonamide; AD-mix-α; ammonia; lithium; lithium triethylborohydride; potassium carbonate; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
2.1: Sharpless asymmetric dihydroxylation / 6.1: Birch reduction;
DOI:10.1016/j.tet.2011.09.066
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 0 °C
2.1: potassium carbonate / methanol / 20 °C
3.1: lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.1: ammonia; lithium / -40 °C
5.1: pyridine / 0 °C
6.1: sodium iodide / acetone / 20 °C / Reflux
7.1: N,N-dimethyl-formamide / 6 h
8.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
8.2: -78 - 0 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; ammonia; lithium; lithium triethylborohydride; potassium carbonate; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
4.1: Birch reduction;
DOI:10.1016/j.tet.2011.09.066
