Technology Process of ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-(t-butyldiphenylsilyloxy)-9-nonenoate
There total 11 articles about ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-(t-butyldiphenylsilyloxy)-9-nonenoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve;
In
dichloromethane;
at 20 ℃;
for 0.5h;
DOI:10.1016/S0040-4020(97)01014-4
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 82 percent / Na / toluene / 16 h / Heating
2.1: 80 percent / aq. HCl / tetrahydrofuran / 3 h / Heating
3.1: 70 percent / LAH / tetrahydrofuran / 12 h / Heating
4.1: 100 percent / NaIO4 / tetrahydrofuran; H2O / 24 h / 20 °C
5.1: 82 percent / benzene / 24 h / Heating
6.1: 85 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C
7.1: 66 percent / imidazole / dimethylformamide / 0.75 h / 20 °C
8.1: DME; Et2Zn / CH2Cl2 / 0.75 h / 0 - 20 °C
8.2: (R,R)-dioxaborolane / CH2Cl2 / 1 h / 0 - 20 °C
9.1: 100 percent / 4 Angstroem molecular sieves; Celite; PDC / CH2Cl2 / 16 h / 20 °C
10.1: LDA / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
10.2: 75 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C
11.1: 80 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 0.5 h / 20 °C
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; 1,2-dimethoxyethane; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; Celite; diethylzinc; sodium; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
1.1: Cyclization / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Oxidation / 5.1: Condensation / 6.1: Luche reduction / 7.1: silylation / 8.1: Metallation / 8.2: Cyclization / 9.1: Oxidation / 10.1: Metallation / 10.2: Addition / 11.1: Oxidation;
DOI:10.1016/S0040-4020(97)01014-4
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 82 percent / benzene / 24 h / Heating
2.1: 85 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C
3.1: 66 percent / imidazole / dimethylformamide / 0.75 h / 20 °C
4.1: DME; Et2Zn / CH2Cl2 / 0.75 h / 0 - 20 °C
4.2: (R,R)-dioxaborolane / CH2Cl2 / 1 h / 0 - 20 °C
5.1: 100 percent / 4 Angstroem molecular sieves; Celite; PDC / CH2Cl2 / 16 h / 20 °C
6.1: LDA / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
6.2: 75 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C
7.1: 80 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 0.5 h / 20 °C
With
1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; 1,2-dimethoxyethane; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; Celite; diethylzinc; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
1.1: Condensation / 2.1: Luche reduction / 3.1: silylation / 4.1: Metallation / 4.2: Cyclization / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Oxidation;
DOI:10.1016/S0040-4020(97)01014-4
