Technology Process of (3S)-(3,4-dimethoxyphenyl)-(4S)-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene
There total 4 articles about (3S)-(3,4-dimethoxyphenyl)-(4S)-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
dimethyl <(3,4-dimethoxyphenyl)methyl>phosphate;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 - 0 ℃;
for 0.333333h;
(1R,2S)-2-(3,4-dimethoxyphenyl)cyclohex-3-enecarbaldehyde;
In
tetrahydrofuran; hexane;
at 0 ℃;
for 2h;
optical yield given as %de;
diastereoselective reaction;
DOI:10.1021/np100942e
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: diethylaluminium chloride / dichloromethane / 0.08 h / -78 °C
2.1: lithium borohydride / tetrahydrofuran; water / 5 h / -20 - 0 °C
2.2: 0 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
3.2: 0.5 h / -78 - 0 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - 0 °C
4.2: 2 h / 0 °C
With
lithium borohydride; n-butyllithium; oxalyl dichloride; diethylaluminium chloride; dimethyl sulfoxide;
In
tetrahydrofuran; hexane; dichloromethane; water;
1.1: Diels-Alder reaction / 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/np100942e
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: dmap; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
2.1: diethylaluminium chloride / dichloromethane / 0.08 h / -78 °C
3.1: lithium borohydride / tetrahydrofuran; water / 5 h / -20 - 0 °C
3.2: 0 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
4.2: 0.5 h / -78 - 0 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - 0 °C
5.2: 2 h / 0 °C
With
dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; diethylaluminium chloride; dimethyl sulfoxide; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; hexane; dichloromethane; water;
2.1: Diels-Alder reaction / 4.1: Swern oxidation / 4.2: Swern oxidation / 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/np100942e
