Technology Process of (5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde
There total 23 articles about (5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde 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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1225377-86-5
(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-10′-(trimethylsilyl)-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde
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1225377-87-6
(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran; 1,4-dioxane;
at 101 ℃;
for 10h;
Inert atmosphere;
DOI:10.1021/ja101956x
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1225377-87-6
(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde
- Guidance literature:
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Multi-step reaction with 7 steps
1: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere
2: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere
3: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere
4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 23 °C / Inert atmosphere
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 23 °C / Inert atmosphere
6: triphenylphosphine; dicarbonylcyclopentadienylcobalt / 1,4-dioxane / 24 h / 140 °C / Inert atmosphere
7: tetrabutyl ammonium fluoride / tetrahydrofuran; 1,4-dioxane / 10 h / 101 °C / Inert atmosphere
With
1H-imidazole; ammonium cerium (IV) nitrate; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(l) chloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water; acetonitrile;
DOI:10.1021/jo400695c
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1225377-87-6
(5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1-Benzyl-16,16′-dimethyl-1,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,15,16,16′,17,17′-octadecahydro[10,11′-bi(5,10b-propano1,7-phenanthroline)]-1′(15′H)-carbaldehyde
- Guidance literature:
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Multi-step reaction with 14 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: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 23 °C / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 23 °C / Inert atmosphere
13.1: triphenylphosphine; dicarbonylcyclopentadienylcobalt / 1,4-dioxane / 24 h / 140 °C / Inert atmosphere
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran; 1,4-dioxane / 10 h / 101 °C / Inert atmosphere
With
1H-imidazole; n-butyllithium; ammonium cerium (IV) nitrate; magnesium(II) perchlorate; dicarbonylcyclopentadienylcobalt; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; lithium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/jo400695c