Technology Process of (11S,9Z,12Z,15Z)-11-[(tert-butyldiphenylsilyl)oxy]octadeca-9,12,15-trienoic acid methyl ester
There total 7 articles about (11S,9Z,12Z,15Z)-11-[(tert-butyldiphenylsilyl)oxy]octadeca-9,12,15-trienoic acid methyl ester which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
(3Z)-3-hexenyltriphenylphosphonium bromide;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran;
at 0 ℃;
for 0.5h;
(Z)-(S)-11-(tert-Butyl-diphenyl-silanyloxy)-12-oxo-dodec-9-enoic acid methyl ester;
In
tetrahydrofuran;
at 0 ℃;
for 4h;
Further stages.;
DOI:10.1021/jo011102q
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / 0 - 20 °C
1.2: 66 percent / tetrahydrofuran / 2 h / 0 °C
2.1: 90 percent / hydrochloric acid / methanol; H2O / 4 h / 0 °C
3.1: 79 percent / triethylamine; 1,8-diazobicyclo[5.4.0]undec-7-ene / CH2Cl2 / 17 h / 20 °C
4.1: 88 percent / 4-dimethylaminopyridine / CH2Cl2 / 22 h / 20 °C
5.1: 89 percent / pyridinium p-toluenesulfonate / ethanol / 10 h / 55 °C
6.1: 88 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 1.25 h / 20 °C
7.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C
7.2: 59 percent / tetrahydrofuran / 4 h / 0 °C
With
hydrogenchloride; dmap; sodium acetate; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water;
1.2: Wittig reaction / 7.2: Wittig reaction;
DOI:10.1021/jo011102q
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 79 percent / triethylamine; 1,8-diazobicyclo[5.4.0]undec-7-ene / CH2Cl2 / 17 h / 20 °C
2.1: 88 percent / 4-dimethylaminopyridine / CH2Cl2 / 22 h / 20 °C
3.1: 89 percent / pyridinium p-toluenesulfonate / ethanol / 10 h / 55 °C
4.1: 88 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 1.25 h / 20 °C
5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C
5.2: 59 percent / tetrahydrofuran / 4 h / 0 °C
With
dmap; sodium acetate; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; dichloromethane;
5.2: Wittig reaction;
DOI:10.1021/jo011102q
