Technology Process of (4R,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol
There total 7 articles about (4R,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-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:
-
With
ammonium chloride; zinc;
In
tetrahydrofuran;
at 0 ℃;
for 3.25h;
Overall yield = 1.8 g;
DOI:10.1016/j.tetlet.2012.11.015
- Guidance literature:
-
Multi-step reaction with 6 steps
1: diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide; titanium(IV)isopropoxide / dichloromethane / 8 h / -30 °C
2: toluene; dichloromethane / 2 h / 0 °C / Inert atmosphere
3: sodium periodate / tetrahydrofuran; water / 2 h / 0 - 20 °C
4: benzene / 3 h / 20 °C
5: diisobutylaluminium hydride / toluene; dichloromethane / 2.33 h / -78 - 20 °C / Inert atmosphere
6: zinc; ammonium chloride / tetrahydrofuran / 3.25 h / 0 °C
With
tert.-butylhydroperoxide; sodium periodate; diethyl (2S,3S)-tartrate; titanium(IV)isopropoxide; diisobutylaluminium hydride; ammonium chloride; zinc;
In
tetrahydrofuran; dichloromethane; water; toluene; benzene;
1: |Sharpless Asymmetric Epoxidation / 4: |Wittig Olefination / 6: |Barbier Coupling Reaction;
DOI:10.1016/j.tetlet.2012.11.015
- Guidance literature:
-
Multi-step reaction with 9 steps
1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C
2: dichloromethane / 2 h / 20 °C
3: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - 20 °C
4: diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide; titanium(IV)isopropoxide / dichloromethane / 8 h / -30 °C
5: toluene; dichloromethane / 2 h / 0 °C / Inert atmosphere
6: sodium periodate / tetrahydrofuran; water / 2 h / 0 - 20 °C
7: benzene / 3 h / 20 °C
8: diisobutylaluminium hydride / toluene; dichloromethane / 2.33 h / -78 - 20 °C / Inert atmosphere
9: zinc; ammonium chloride / tetrahydrofuran / 3.25 h / 0 °C
With
tert.-butylhydroperoxide; sodium periodate; dipyridinium dichromate; diethyl (2S,3S)-tartrate; titanium(IV)isopropoxide; diisobutylaluminium hydride; ammonium chloride; zinc;
In
tetrahydrofuran; dichloromethane; water; toluene; benzene;
4: |Sharpless Asymmetric Epoxidation / 7: |Wittig Olefination / 9: |Barbier Coupling Reaction;
DOI:10.1016/j.tetlet.2012.11.015
