Technology Process of (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone
There total 16 articles about (2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane;
With
3-chloro-benzenecarboperoxoic acid;
In
dichloromethane;
at 20 ℃;
for 0.25h;
With
periodic acid;
In
diethyl ether;
for 2h;
DOI:10.1002/anie.201108223
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C
2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
3.1: dichloromethane / 20 h
4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere
5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice
6.2: 0.25 h
7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere
9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C
9.2: 2 h
With
pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
2.1: dichloromethane / 20 h
3.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere
4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice
5.2: 0.25 h
6.1: pyrrolidine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C
8.2: 2 h
With
pyrrolidine; tetrakis(triphenylphosphine) palladium(0); carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
1.1: Dess-Martin oxidation / 2.1: Wittig reaction / 6.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223
