Technology Process of <1R-(1α,2α,4αβ,8aα)>-1-benzyloxymethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,2,3,4,6,7-hexahydro-<8aH>-naphthalen-8-one
There total 13 articles about <1R-(1α,2α,4αβ,8aα)>-1-benzyloxymethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,2,3,4,6,7-hexahydro-<8aH>-naphthalen-8-one 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 11 steps
1: 1.) pig liver esterase / 1.) water, room t., pH=7; 2.) ether
2: 93 percent / p-toluenesulfonic acid / toluene / 2 h / Heating
3: 92 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature
4: 90 percent / sodium hydride, tetrabutyl ammonium iodide / tetrahydrofuran / 24 h / Ambient temperature
5: 80 percent / 5percent HCl / tetrahydrofuran / 12 h / Ambient temperature
6: 1.) LDA, chlorotrimethylsilane; 2.) Pd(OAc)2, p-benzoquinone / 1.) THF, from -78 degC to room t. over 1 h; 2.) acetonitrile, room t., 6 h
7: 83 percent / potassium tert-butoxide / tetrahydrofuran / 36 h / Ambient temperature
8: 60.8 percent / HCl / ethanol / 2.5 h / Heating
9: 99.8 percent / CeCl3*6H2O, NaBH4 / methanol / 0.17 h / Ambient temperature
10: 23 percent / hydrogen peroxide, potassium carbonate / methanol / 15 h / Ambient temperature
11: 80 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / Ambient temperature
With
hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; chloro-trimethyl-silane; pig liver esterase; cerium(III) chloride; potassium tert-butylate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)85667-2
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 90 percent / sodium hydride, tetrabutyl ammonium iodide / tetrahydrofuran / 24 h / Ambient temperature
2: 80 percent / 5percent HCl / tetrahydrofuran / 12 h / Ambient temperature
3: 1.) LDA, chlorotrimethylsilane; 2.) Pd(OAc)2, p-benzoquinone / 1.) THF, from -78 degC to room t. over 1 h; 2.) acetonitrile, room t., 6 h
4: 83 percent / potassium tert-butoxide / tetrahydrofuran / 36 h / Ambient temperature
5: 60.8 percent / HCl / ethanol / 2.5 h / Heating
6: 99.8 percent / CeCl3*6H2O, NaBH4 / methanol / 0.17 h / Ambient temperature
7: 23 percent / hydrogen peroxide, potassium carbonate / methanol / 15 h / Ambient temperature
8: 80 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / Ambient temperature
With
hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; chloro-trimethyl-silane; cerium(III) chloride; potassium tert-butylate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)85667-2
