Technology Process of (4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol
There total 7 articles about (4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
allylmagnesium bromide;
With
B-chlorodiisopinocampheylborane;
In
diethyl ether;
for 1h;
C36H38O5;
at -100 - -80 ℃;
for 3h;
Overall yield = 0.35 g; diastereoselective reaction;
DOI:10.1016/j.tetlet.2013.12.061
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 3 h / -78 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
4.1: B-chlorodiisopinocampheylborane / diethyl ether / 1 h
4.2: 3 h / -100 - -80 °C
With
oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; B-chlorodiisopinocampheylborane;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
1.1: |Swern Oxidation / 2.1: |Still-Gennary Z-Olefination;
DOI:10.1016/j.tetlet.2013.12.061
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
2.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 3 h / -78 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
5.1: B-chlorodiisopinocampheylborane / diethyl ether / 1 h
5.2: 3 h / -100 - -80 °C
With
oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; B-chlorodiisopinocampheylborane;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
2.1: |Swern Oxidation / 3.1: |Still-Gennary Z-Olefination;
DOI:10.1016/j.tetlet.2013.12.061
