Technology Process of (4aR,5S,10bR,12R)-1-benzyl-8-((tert-butyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
There total 11 articles about (4aR,5S,10bR,12R)-1-benzyl-8-((tert-butyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 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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1225377-78-5
(4aR,5S,10bR,12R)-1-benzyl-8-ethynyl-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
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1438285-60-9
(4aR,5S,10bR,12R)-1-benzyl-8-((tert-butyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
- Guidance literature:
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With
lithium hexamethyldisilazane;
In
tetrahydrofuran; toluene;
at 0 ℃;
for 3h;
Inert atmosphere;
DOI:10.1021/jo400695c
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1438285-60-9
(4aR,5S,10bR,12R)-1-benzyl-8-((tert-butyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
- Guidance literature:
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Multi-step reaction with 13 steps
1.1: lithium hydroxide; water / methanol / 23 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran / 66 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.08 h / 0 °C / Inert atmosphere
3.2: 70 h / 23 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 11 h / -78 - 23 °C / Inert atmosphere
5.1: n-butyllithium / diethyl ether; hexane / 0.68 h / -78 °C / Inert atmosphere
5.2: 0.55 h / -78 °C / Inert atmosphere
6.1: tetrahydrofuran; toluene / 0.58 h / 23 °C / Inert atmosphere
7.1: magnesium(II) perchlorate / 0.5 h / 23 °C / Inert atmosphere
8.1: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere
9.1: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere
10.1: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere
11.1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 20 h / 140 °C / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 23 °C / Inert atmosphere; Heating
13.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 3 h / 0 °C / Inert atmosphere
With
1H-imidazole; n-butyllithium; magnesium(II) perchlorate; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; lithium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jo400695c
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1438285-60-9
(4aR,5S,10bR,12R)-1-benzyl-8-((tert-butyldimethylsilyl)ethynyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
- Guidance literature:
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Multi-step reaction with 4 steps
1: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere
2: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 20 h / 140 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 23 °C / Inert atmosphere; Heating
4: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 3 h / 0 °C / Inert atmosphere
With
1H-imidazole; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; tetrachloromethane; toluene;
DOI:10.1021/jo400695c
