Technology Process of (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether
There total 8 articles about (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide;
With
phenyllithium;
In
tetrahydrofuran; diethyl ether; cyclohexane;
at -20 ℃;
for 0.5h;
Inert atmosphere;
(20R)-des-A,B-20-butylpregnan-8-one;
In
tetrahydrofuran; diethyl ether; cyclohexane;
at -78 - 4 ℃;
for 24h;
Inert atmosphere;
DOI:10.1016/j.bioorg.2013.01.001
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C
2.1: potassium iodide / acetone / 18 h / Reflux
3.1: pyridine; nickel(II) chloride hexahydrate; zinc / 2 h / 50 - 65 °C
3.2: 0 - 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C
5.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C
7.1: pyridinium p-toluenesulfonate; pyridinium dichromate / dichloromethane / 5 h / 20 °C
8.1: phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / -20 °C / Inert atmosphere
8.2: 24 h / -78 - 4 °C / Inert atmosphere
With
pyridine; dmap; lithium aluminium tetrahydride; pyridinium dichromate; nickel(II) chloride hexahydrate; pyridinium p-toluenesulfonate; phenyllithium; triethylamine; potassium iodide; zinc;
In
tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetone;
DOI:10.1016/j.bioorg.2013.01.001
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C
2.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C
4.1: pyridinium p-toluenesulfonate; pyridinium dichromate / dichloromethane / 5 h / 20 °C
5.1: phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / -20 °C / Inert atmosphere
5.2: 24 h / -78 - 4 °C / Inert atmosphere
With
dmap; lithium aluminium tetrahydride; pyridinium dichromate; pyridinium p-toluenesulfonate; phenyllithium; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane;
DOI:10.1016/j.bioorg.2013.01.001
