Technology Process of (6Z,8E,10E)-(5S,12S)-5,12-Bis-(tert-butyl-dimethyl-silanyloxy)-13-phenoxy-trideca-6,8,10-trienoic acid
There total 13 articles about (6Z,8E,10E)-(5S,12S)-5,12-Bis-(tert-butyl-dimethyl-silanyloxy)-13-phenoxy-trideca-6,8,10-trienoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 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
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; dimethylsulfide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; methyllithium; bis-(1,2-dimethylpropyl)borane; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride;
tetrakis(triphenylphosphine) palladium(0);
In
dichloromethane; toluene;
DOI:10.1021/jo00306a007
- Guidance literature:
-
Multi-step reaction with 8 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
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 4 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
With
1H-imidazole; propylamine; potassium cyanide; lithium hydroxide; bis-(1,2-dimethylpropyl)borane; silver nitrate;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00306a007
