Technology Process of (3Z,7E)-(5S)-9-(tert-butyldiphenylsilanyloxy)-3,5,7-trimethylocta-3,7-dien-1-yne
There total 6 articles about (3Z,7E)-(5S)-9-(tert-butyldiphenylsilanyloxy)-3,5,7-trimethylocta-3,7-dien-1-yne which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2Z,6E)-(4S)-8-(tert-butyldiphenylsilanyloxy)-2,4,6-trimethylocta-2,6-dienal; carbon tetrabromide;
With
triphenylphosphine;
In
dichloromethane;
at 0 ℃;
for 0.166667h;
With
n-butyllithium;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
Further stages.;
DOI:10.1021/ol015753k
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 2 h / -78 °C
2.1: 98 percent / DIBAL / diethyl ether / 1.5 h / -78 - 20 °C
3.1: oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.75 h / -78 °C
4.1: triphenylphosphine / CH2Cl2 / 0.17 h / 0 °C
4.2: 1.05 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C
With
oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol015753k
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -78 °C
2.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 2 h / -78 °C
3.1: 98 percent / DIBAL / diethyl ether / 1.5 h / -78 - 20 °C
4.1: oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.75 h / -78 °C
5.1: triphenylphosphine / CH2Cl2 / 0.17 h / 0 °C
5.2: 1.05 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C
With
oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene;
1.1: Swern oxidation;
DOI:10.1021/ol015753k
