Technology Process of (4R,5E,8S,10R,11E)-8,10-bis{[tert-butyl(dimethyl)silyl]oxy}-12-phenyldodeca-1,5,11-trien-4-ol
There total 6 articles about (4R,5E,8S,10R,11E)-8,10-bis{[tert-butyl(dimethyl)silyl]oxy}-12-phenyldodeca-1,5,11-trien-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(+)-allylbis(isopinocampheyl)borane; (2E,8E)-(5S,7R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-phenyl-nona-2,8-dienal;
In
diethyl ether; pentane;
at -100 - 0 ℃;
Inert atmosphere;
With
dihydrogen peroxide; sodium hydroxide;
In
diethyl ether; water; pentane;
DOI:10.1055/s-0031-1290771
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere
1.2: 0.17 h / 0 °C / Inert atmosphere
1.3: 0.25 h / -78 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.25 h / -78 °C / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.33 h / 20 °C / Inert atmosphere
4.2: 1 h / 20 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere
6.1: diethyl ether; pentane / -100 - 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium tetrachloride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; pentane;
4.2: Horner-Wadsworth-Emmons olefination / 6.1: Brown allylation / 6.2: Brown allylation;
DOI:10.1055/s-0031-1290771
- Guidance literature:
-
Multi-step reaction with 2 steps
1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere
2: diethyl ether; pentane / -100 - 0 °C / Inert atmosphere
With
diisobutylaluminium hydride;
In
tetrahydrofuran; diethyl ether; toluene; pentane;
2: Brown allylation / 2: Brown allylation;
DOI:10.1055/s-0031-1290771
