Technology Process of (3Z,5Z,7Z)-19,19,20,20,20-pentadeuterio-1-(tert-butyldiphenylsiloxy)pentadeca-3,5,7-trien-1-ol
There total 14 articles about (3Z,5Z,7Z)-19,19,20,20,20-pentadeuterio-1-(tert-butyldiphenylsiloxy)pentadeca-3,5,7-trien-1-ol 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:
-
Multi-step reaction with 6 steps
1: 98 percent / imidazole / 12 h / 25 °C
2: 1.) n-BuLi, 2.) D2O / 1.) THF, hexane, -78 deg C, 45 min, 2.) from -78 deg C to RT, 1 h
3: 100 percent / D2 (99.5percent) / Rh on alumina / tetrahydrofuran / 12 h / 25 °C
4: 95 percent / n-Bu4NF / tetrahydrofuran / 4 h / 0 - 25 °C
5: 85 percent / CrO3, pyridine / CH2Cl2 / 0.5 h / 25 °C
6: 1.) NaN3)3>2 / 1.) DME, THF, -35 deg C, 45 min, 2.) -35 deg C, 45 min
With
pyridine; 1H-imidazole; chromium(VI) oxide; n-butyllithium; tetrabutyl ammonium fluoride; water-d2; sodium hexamethyldisilazane; deuterium;
rhodium on alumina;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00284a025
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 1.) n-BuLi, 2.) D2O / 1.) THF, hexane, -78 deg C, 45 min, 2.) from -78 deg C to RT, 1 h
2: 100 percent / D2 (99.5percent) / Rh on alumina / tetrahydrofuran / 12 h / 25 °C
3: 95 percent / n-Bu4NF / tetrahydrofuran / 4 h / 0 - 25 °C
4: 85 percent / CrO3, pyridine / CH2Cl2 / 0.5 h / 25 °C
5: 1.) NaN3)3>2 / 1.) DME, THF, -35 deg C, 45 min, 2.) -35 deg C, 45 min
With
pyridine; chromium(VI) oxide; n-butyllithium; tetrabutyl ammonium fluoride; water-d2; sodium hexamethyldisilazane; deuterium;
rhodium on alumina;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00284a025
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) from -78 deg C to 25 deg C, 12 h
2: 96 percent / KOH / diethyl ether / 1 h / -20 - 0 °C
3: 1.) a) EtMgBr, b) CuI / 1.) a) THF, 65 deg C, 1 h, b) 0 deg C, 30 min, 2.) 0 deg C, 30 min
4: 73 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 25 °C
5: 99 percent / H2 / Lindlar catalyst / hexane; CH2Cl2 / 10 h / 25 °C
6: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.75 h / -40 - -30 °C
7: 97 percent / acetonitrile / 12 h / Heating
8: 1.) NaN3)3>2 / 1.) DME, THF, -35 deg C, 45 min, 2.) -35 deg C, 45 min
With
potassium hydroxide; copper(l) iodide; n-butyllithium; carbon tetrabromide; ethylmagnesium bromide; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; triphenylphosphine;
Lindlar's catalyst;
In
methanol; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo00284a025
