Technology Process of (1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene
There total 22 articles about (1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene 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:
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![(1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene](/Databaselist/images/loading.webp)
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266675-90-5
(1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene
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(1R,3S,4aR,5R,7Z,8aS)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene
- Guidance literature:
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In
benzene;
at 80 ℃;
for 18h;
DOI:10.1021/ol9904085
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266675-90-5
(1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene
- Guidance literature:
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Multi-step reaction with 21 steps
1.1: TfOH / diethyl ether / 20 °C
2.1: nBuLi / tetrahydrofuran / -78 - 20 °C
3.1: tetrahydrofuran / -45 °C
4.1: LiAlH4 / diethyl ether / 0 °C
5.1: MnO2 / CH2Cl2
5.2: 74 percent / Bu2BOTf; Et3N / CH2Cl2 / -78 °C
6.1: 86 percent / LiBH4; MeOH / diethyl ether
7.1: 84 percent / Et3N; DMAP / CH2Cl2
8.1: 89 percent / p-xylene / 100 °C
9.1: LiAl(nBu)iBu2H / tetrahydrofuran / 20 °C
10.1: (+)-(lpc)2BOCH3 / diethyl ether / -78 °C
11.1: 86 percent / iPr2NEt / CH2Cl2
12.1: 79 percent / OsO4; NMO; H2O / acetone; 2-methyl-propan-2-ol
13.1: TsOH / dimethylformamide / 20 °C
14.1: TBAF / tetrahydrofuran / 20 °C
15.1: Et3N; DMAP / CH2Cl2
16.1: KOtBu / tetrahydrofuran / 0 - 20 °C
17.1: aq. AcOH
18.1: aq. NaIO4 / tetrahydrofuran
19.1: KF / propan-2-ol
20.1: 64 percent / DCC; CuI / diethyl ether
21.1: 84 percent / benzene / 18 h / 80 °C
With
methanol; dmap; manganese(IV) oxide; potassium fluoride; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; lithium n-butyldiisobutylaluminum hydride; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane;
In
tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol; benzene;
1.1: Substitution / 2.1: Substitution / 3.1: Addition / 4.1: Reduction / 5.1: Oxidation / 5.2: Evans aldolization / 6.1: cleavage / 7.1: silylation / 8.1: Eschenmoser-Claisen rearrangement / 9.1: Reduction / 10.1: Grignard reaction / 11.1: Etherification / 12.1: Oxidation / 13.1: Etherification / 14.1: desilylation / 15.1: Substitution / 16.1: Elimination / 17.1: Hydrolysis / 18.1: oxidative cleavage / 19.1: aldol condensation / 20.1: Dehydration / 21.1: Cycloaddition;
DOI:10.1021/ol9904085
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266675-90-5
(1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene
- Guidance literature:
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Multi-step reaction with 20 steps
1.1: nBuLi / tetrahydrofuran / -78 - 20 °C
2.1: tetrahydrofuran / -45 °C
3.1: LiAlH4 / diethyl ether / 0 °C
4.1: MnO2 / CH2Cl2
4.2: 74 percent / Bu2BOTf; Et3N / CH2Cl2 / -78 °C
5.1: 86 percent / LiBH4; MeOH / diethyl ether
6.1: 84 percent / Et3N; DMAP / CH2Cl2
7.1: 89 percent / p-xylene / 100 °C
8.1: LiAl(nBu)iBu2H / tetrahydrofuran / 20 °C
9.1: (+)-(lpc)2BOCH3 / diethyl ether / -78 °C
10.1: 86 percent / iPr2NEt / CH2Cl2
11.1: 79 percent / OsO4; NMO; H2O / acetone; 2-methyl-propan-2-ol
12.1: TsOH / dimethylformamide / 20 °C
13.1: TBAF / tetrahydrofuran / 20 °C
14.1: Et3N; DMAP / CH2Cl2
15.1: KOtBu / tetrahydrofuran / 0 - 20 °C
16.1: aq. AcOH
17.1: aq. NaIO4 / tetrahydrofuran
18.1: KF / propan-2-ol
19.1: 64 percent / DCC; CuI / diethyl ether
20.1: 84 percent / benzene / 18 h / 80 °C
With
methanol; dmap; manganese(IV) oxide; potassium fluoride; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; lithium n-butyldiisobutylaluminum hydride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane;
In
tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol; benzene;
1.1: Substitution / 2.1: Addition / 3.1: Reduction / 4.1: Oxidation / 4.2: Evans aldolization / 5.1: cleavage / 6.1: silylation / 7.1: Eschenmoser-Claisen rearrangement / 8.1: Reduction / 9.1: Grignard reaction / 10.1: Etherification / 11.1: Oxidation / 12.1: Etherification / 13.1: desilylation / 14.1: Substitution / 15.1: Elimination / 16.1: Hydrolysis / 17.1: oxidative cleavage / 18.1: aldol condensation / 19.1: Dehydration / 20.1: Cycloaddition;
DOI:10.1021/ol9904085
