Technology Process of 5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-8,13-dienal
There total 16 articles about 5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-8,13-dienal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
dipyridinium dichromate; 4 A molecular sieve;
In
dichloromethane;
DOI:10.1021/ja0015287
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 100 percent / 2,6-lutidine / CH2Cl2 / 1.5 h
2.1: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C
3.1: n-BuLi / tetrahydrofuran
4.1: t-BuLi / diethyl ether / 0.17 h / -78 °C
4.2: MgBr2 / diethyl ether
4.3: 14 percent / PdCl2(dppf) / diethyl ether / 20 °C
5.1: 98 percent / DDQ; H2O / CH2Cl2 / 3 h
6.1: I2; PPh3; imidazole / benzene; diethyl ether / 2 h
7.1: i-Pr2NEt / 24 h / 80 °C
8.1: KHMDS / toluene / 0 °C
8.2: 57 percent / toluene / -78 - 10 °C
9.1: 74 percent / DIBAL / CH2Cl2 / 0 °C
10.1: 86 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH2Cl2
With
1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; water; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; benzene;
1.1: silylation / 2.1: Reduction / 3.1: Condensation / 4.1: Metallation / 4.2: transmetallation / 4.3: Substitution / 5.1: ether cleavage / 6.1: Iodination / 7.1: Cyclization / 8.1: Metallation / 8.2: Wittig condensation / 9.1: Ring cleavage / 10.1: Oxidation;
DOI:10.1021/ja0015287
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: n-BuLi / tetrahydrofuran
2.1: t-BuLi / diethyl ether / 0.17 h / -78 °C
2.2: MgBr2 / diethyl ether
2.3: 14 percent / PdCl2(dppf) / diethyl ether / 20 °C
3.1: 98 percent / DDQ; H2O / CH2Cl2 / 3 h
4.1: I2; PPh3; imidazole / benzene; diethyl ether / 2 h
5.1: i-Pr2NEt / 24 h / 80 °C
6.1: KHMDS / toluene / 0 °C
6.2: 57 percent / toluene / -78 - 10 °C
7.1: 74 percent / DIBAL / CH2Cl2 / 0 °C
8.1: 86 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH2Cl2
With
1H-imidazole; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; water; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene;
1.1: Condensation / 2.1: Metallation / 2.2: transmetallation / 2.3: Substitution / 3.1: ether cleavage / 4.1: Iodination / 5.1: Cyclization / 6.1: Metallation / 6.2: Wittig condensation / 7.1: Ring cleavage / 8.1: Oxidation;
DOI:10.1021/ja0015287
![4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-16-hydroxy-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-3,8-dienyl]-tetrahydro-pyran-2-ol](/Databaselist/images/loading.webp)
