Technology Process of (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran
There total 13 articles about (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran 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:
-
4-bromo-1-methyl-2-(4-propoxybenzyl)benzene;
With
n-butyllithium;
In
tetrahydrofuran; hexane; toluene;
at -78 ℃;
for 1h;
Inert atmosphere;
(3R,4R,6S)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one;
In
tetrahydrofuran; hexane; toluene;
at -98 ℃;
for 3h;
stereoselective reaction;
Further stages;
DOI:10.1016/j.tetlet.2012.02.062
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 12 h / 130 °C
2.1: methanol; potassium carbonate / 8 h / 20 °C
3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C
4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C
4.2: 0 - 20 °C
5.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 48 h / 20 °C
6.1: di(n-butyl)tin oxide / toluene / 6 h / Reflux
6.2: 16 h / Reflux
7.1: tetrabutyl ammonium fluoride / 0 - 20 °C
8.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C / Inert atmosphere
9.2: 3 h / -98 °C
With
methanol; dmap; potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; mineral oil;
DOI:10.1016/j.tetlet.2012.02.062
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C
1.2: 0 - 20 °C
2.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 48 h / 20 °C
3.1: di(n-butyl)tin oxide / toluene / 6 h / Reflux
3.2: 16 h / Reflux
4.1: tetrabutyl ammonium fluoride / 0 - 20 °C
5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C / Inert atmosphere
6.2: 3 h / -98 °C
With
potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; mineral oil;
DOI:10.1016/j.tetlet.2012.02.062
