Technology Process of (1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol
There total 9 articles about (1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol 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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481656-29-5
(1R,2S,4aS,8aR)-2-[(1β,2β,4aβ,5-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol
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481656-13-7
(1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol
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481656-12-6
(1R,2S,4aS,5R,6S,8aS)-2-[(5β,6β-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol
- Guidance literature:
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With
sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid;
In
dichloromethane;
at 0 ℃;
for 1h;
DOI:10.1002/ejoc.201100173
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481656-13-7
(1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: lithium; liquid ammonia / tetrahydrofuran / 1 h / Heating
1.2: 72 percent / tetrahydrofuran / 2 h / 20 °C
2.1: 86 percent / potassium tert-butoxide / benzene / 12 h / Heating
3.1: 97 percent / 4M HCl / tetrahydrofuran / 2 h / 20 °C
4.1: 80 percent / hydrogen; triethylamine / 10percent Pd/C / methanol / 16 h / 20 °C / 760.05 Torr
5.1: 100 percent / potassium tert-butoxide / benzene / 12 h / Heating
6.1: 100 percent / RhCl3*3H2O / ethanol / 23 h / Heating
7.1: 84 percent / lithium n-butylthiolate / hexamethylphosphoric acid triamide / 2 h / 110 °C
8.1: 75 percent / m-chloroperbenzoic acid; sodium hydrogen carbonate / CH2Cl2 / 1 h / 0 °C
With
hydrogenchloride; rhodium(III) chloride; potassium tert-butylate; ammonia; hydrogen; lithium; sodium hydrogencarbonate; lithium-n-butanethiolate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
10percent Pd/C;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene;
2.1: Wittig reaction / 5.1: Wittig reaction;
DOI:10.1021/ol0271032
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481656-13-7
(1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: lithium; liquid ammonia / tetrahydrofuran / 1 h / Heating
1.2: 72 percent / tetrahydrofuran / 2 h / 20 °C
2.1: 86 percent / potassium tert-butoxide / benzene / 12 h / Heating
3.1: 97 percent / 4M HCl / tetrahydrofuran / 2 h / 20 °C
4.1: 80 percent / hydrogen; triethylamine / 10percent Pd/C / methanol / 16 h / 20 °C / 760.05 Torr
5.1: 100 percent / potassium tert-butoxide / benzene / 12 h / Heating
6.1: 100 percent / RhCl3*3H2O / ethanol / 23 h / Heating
7.1: 84 percent / lithium n-butylthiolate / hexamethylphosphoric acid triamide / 2 h / 110 °C
8.1: 75 percent / m-chloroperbenzoic acid; sodium hydrogen carbonate / CH2Cl2 / 1 h / 0 °C
With
hydrogenchloride; rhodium(III) chloride; potassium tert-butylate; ammonia; hydrogen; lithium; sodium hydrogencarbonate; lithium-n-butanethiolate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
10percent Pd/C;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene;
2.1: Wittig reaction / 5.1: Wittig reaction;
DOI:10.1021/ol0271032