Technology Process of (2E,6E,10E,14R)-ethyl 14-hydroxy-16-(2,5-dihydroxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,6,10-trienoate
There total 23 articles about (2E,6E,10E,14R)-ethyl 14-hydroxy-16-(2,5-dihydroxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,6,10-trienoate 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:
-
With
ammonium cerium(IV) nitrate; water;
In
tetrahydrofuran;
at 0 ℃;
for 0.666667h;
DOI:10.1021/ol051849t
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 85 percent / toluene / 0.5 h / 90 °C
2: 81 percent / t-BuLi; 9-MeO-9-BBN; K3PO4 / Pd(dppf)Cl2; DMF / diethyl ether; hexane; pentane / 2 h / 20 °C
3: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C
4: CAN; H2O / tetrahydrofuran / 0.67 h / 0 °C
With
potassium phosphate; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; 9-methoxy-9-BBN;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N,N-dimethyl-formamide;
In
tetrahydrofuran; diethyl ether; hexane; toluene; pentane;
1: Wittig reaction / 2: Suzuki coupling;
DOI:10.1021/ol051849t
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 99 percent / H2; KOAc / Pd(OH)2/C / ethyl acetate / 1 h
2: 96 percent / NaH / tetrahydrofuran / 0 - 20 °C
3: 93 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C
4: Ti(O-i-Pr)4; (+)-diethyl tartrate; 4 Angstroem molecular sieves / tert-butyl hydroperoxide / CH2Cl2 / 1.5 h / -20 °C
5: 0.48 g / Red-Al / tetrahydrofuran; toluene / 0 - 20 °C
6: 85 percent / Et3N / CH2Cl2 / 1 h / 0 °C
7: 96 percent / NaI / acetone / 5 h / Heating
8: 91 percent / 4 Angstroem molecular sieves; 2,6-lutidine / CH2Cl2 / 0 - 20 °C
9: 81 percent / t-BuLi; 9-MeO-9-BBN; K3PO4 / Pd(dppf)Cl2; DMF / diethyl ether; hexane; pentane / 2 h / 20 °C
10: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C
11: CAN; H2O / tetrahydrofuran / 0.67 h / 0 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; potassium phosphate; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; potassium acetate; sodium hydride; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; triethylamine; 9-methoxy-9-BBN; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide;
tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium dihydroxide; N,N-dimethyl-formamide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; pentane;
2: Horner-Emmons olefination / 4: Sharpless epoxidation / 9: Suzuki coupling;
DOI:10.1021/ol051849t
