Technology Process of <1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester
There total 16 articles about <1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester which
guide to synthetic route it.
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synthetic route:
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160062-71-5
<1R-(1α,2α,4αβ,8β,8aα)>-1-benzyloxymethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-4-ol
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160062-72-6
<1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester
- Guidance literature:
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With
dmap; dicyclohexyl-carbodiimide;
In
dichloromethane;
for 24h;
Ambient temperature;
DOI:10.1016/S0040-4020(01)85667-2
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160062-72-6
<1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester
- Guidance literature:
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Multi-step reaction with 13 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
12: 75 percent / lithium aluminum tri-tert-butoxide hydride / tetrahydrofuran / 6 h / Ambient temperature
13: 85 percent / dicyclohexylcarbodiimide, 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; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)85667-2
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160062-72-6
<1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester
- Guidance literature:
-
Multi-step reaction with 10 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
9: 75 percent / lithium aluminum tri-tert-butoxide hydride / tetrahydrofuran / 6 h / Ambient temperature
10: 85 percent / dicyclohexylcarbodiimide, 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; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)85667-2
