Technology Process of 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid
There total 14 articles about 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid 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 7 steps
1: 1) O3, 2) dimethyl sulfide / 1) MeOH, -78 deg C, 2) -78 deg C to RT, 1.5h
2: 1) MeLi / 1) Et2O, 0 deg C, 30 min, 2) 0 deg C, 30 min
3: 95 percent / <(CH3O(CH2)2O)2AlH2>Na / toluene / Heating
4: 47 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2
6: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 2) THF
7: 84 percent / n-Bu4NF / tetrahydrofuran
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; dimethylsulfide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyllithium; bis-(1,2-dimethylpropyl)borane; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo00306a007
- Guidance literature:
-
Multi-step reaction with 9 steps
2: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C
3: Br2 / CH2Cl2 / 0.17 h / -70 °C
4: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C
5: imidazole / dimethylformamide / 5 h / Ambient temperature
6: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature
7: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min
8: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 2) THF
9: 84 percent / n-Bu4NF / tetrahydrofuran
With
1H-imidazole; titanium(IV) isopropylate; propylamine; tert.-butylhydroperoxide; potassium cyanide; lithium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; bromine; bis-(1,2-dimethylpropyl)borane; D-(-)-diisopropyl tartrate; silver nitrate;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00306a007
- Guidance literature:
-
Multi-step reaction with 5 steps
1: imidazole / dimethylformamide / 5 h / Ambient temperature
2: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature
3: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min
4: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 2) THF
5: 84 percent / n-Bu4NF / tetrahydrofuran
With
1H-imidazole; propylamine; potassium cyanide; lithium hydroxide; tetrabutyl ammonium fluoride; bis-(1,2-dimethylpropyl)borane; silver nitrate;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00306a007
