Technology Process of 13-(tert-butyl-diphenyl-silanyloxy)-11-(tetrahydro-pyran-2-yloxy)-tridecan-1-ol
There total 7 articles about 13-(tert-butyl-diphenyl-silanyloxy)-11-(tetrahydro-pyran-2-yloxy)-tridecan-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
tert-butyl-diphenyl-[3-(tetrahydro-pyran-2-yloxy)-tridec-12-enyloxy]-silane;
With
dimethylsulfide borane complex;
In
tetrahydrofuran;
at 0 ℃;
With
sodium hydroxide; dihydrogen peroxide;
In
tetrahydrofuran; water;
at 0 - 20 ℃;
DOI:10.1021/ol034338k
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: NaH / tetrahydrofuran / 0 °C
2.1: i-Bu2AlH / CH2Cl2 / -78 °C
3.1: 82 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH2Cl2 / -23 °C
4.1: Red-Al / tetrahydrofuran / 0 - 20 °C
4.2: 76 percent / NaIO4 / CH2Cl2; acetone; H2O
5.1: 99 percent / imidazole / dimethylformamide / 0 °C
6.1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 20 °C
7.1: BH3*SMe2 / tetrahydrofuran / 0 °C
7.2: 87 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0 - 20 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride;
4 A molecular sieve;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
1.1: Wittig reaction / 3.1: Sharpless epoxidation;
DOI:10.1021/ol034338k
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: i-Bu2AlH / CH2Cl2 / -78 °C
2.1: 82 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; t-butyl hydroperoxide / molecular sieves 4 Angstroem / CH2Cl2 / -23 °C
3.1: Red-Al / tetrahydrofuran / 0 - 20 °C
3.2: 76 percent / NaIO4 / CH2Cl2; acetone; H2O
4.1: 99 percent / imidazole / dimethylformamide / 0 °C
5.1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 20 °C
6.1: BH3*SMe2 / tetrahydrofuran / 0 °C
6.2: 87 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0 - 20 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (-)-diethyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride;
4 A molecular sieve;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
2.1: Sharpless epoxidation;
DOI:10.1021/ol034338k