Technology Process of (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-butylazocane
There total 10 articles about (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-butylazocane 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:
- Guidance literature:
-
With
sodium tris(acetoxy)borohydride;
In
1,2-dichloro-ethane;
at 20 ℃;
for 16h;
Inert atmosphere;
DOI:10.1021/jo202054g
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-
(3S,4S,5R,Z)-3,4,5-tris(benzyloxy)-1-tosyl-1,2,3,4,5,8-hexahydroazocine
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: water; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tetrahydrofuran; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere
1.2: K2OsO2(OH)4 / 40 h / 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere
3.1: naphthalene; sodium / 1,2-dimethoxyethane / 0.5 h / -78 °C / Inert atmosphere
4.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere
With
naphthalene; water; sodium; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; 1,2-dimethoxyethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
1.1: Sharpless cis-asymmetric dihydroxylation / 1.2: Sharpless cis-asymmetric dihydroxylation;
DOI:10.1021/jo202054g
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux
3.1: water; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tetrahydrofuran; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere
3.2: K2OsO2(OH)4 / 40 h / 20 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere
5.1: naphthalene; sodium / 1,2-dimethoxyethane / 0.5 h / -78 °C / Inert atmosphere
6.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; naphthalene; water; sodium; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
3.1: Sharpless cis-asymmetric dihydroxylation / 3.2: Sharpless cis-asymmetric dihydroxylation;
DOI:10.1021/jo202054g
