Technology Process of (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)-5-(trityloxy)non-1-en-4-ol
There total 10 articles about (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)-5-(trityloxy)non-1-en-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
vinyl magnesium bromide;
With
copper(I) bromide dimethylsulfide complex; dimethylsulfide;
In
tetrahydrofuran; diethyl ether;
at -15 - 0 ℃;
for 1h;
Inert atmosphere;
tert-butyl-((R)-4-(naphthalen-2-ylmethoxy)methyl-3-(((2R,3R)-3-(trityloxymethyl)oxiran-2-yl)methyl)butoxy)diphenylsilane;
In
tetrahydrofuran; diethyl ether;
at 20 ℃;
for 18h;
Inert atmosphere;
DOI:10.3762/bjoc.9.132
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: sodium hydride; tetra-(n-butyl)ammonium iodide; 1H-imidazole / tetrahydrofuran / 0 °C
2.1: Shi's ketone; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide; acetic acid; edetate disodium / acetonitrile; water / 9 h / 20 °C
3.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran; diethyl ether / 1 h / -15 - 0 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
With
1H-imidazole; Shi's ketone; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; potassium hydroxide;
In
tetrahydrofuran; diethyl ether; water; acetonitrile;
2.1: |Shi Asymmetric Epoxidation / 3.2: |Payne Rearrangement;
DOI:10.3762/bjoc.9.132
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: sodium hydride; tetra-(n-butyl)ammonium iodide; 1H-imidazole / tetrahydrofuran / 0 °C
2.1: Shi's ketone; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide; acetic acid; edetate disodium / acetonitrile; water / 9 h / 20 °C
3.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran; diethyl ether / 1 h / -15 - 0 °C / Inert atmosphere
3.2: 18 h / 20 °C / Inert atmosphere
With
1H-imidazole; Shi's ketone; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; potassium hydroxide;
In
tetrahydrofuran; diethyl ether; water; acetonitrile;
2.1: |Shi Asymmetric Epoxidation / 3.2: |Payne Rearrangement;
DOI:10.3762/bjoc.9.132
