Technology Process of (1S,5R,7S)-7-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,6-dioxabicyclo[3.3.1]nonan-3-one
There total 10 articles about (1S,5R,7S)-7-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,6-dioxabicyclo[3.3.1]nonan-3-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid;
With
2,4,6-trichlorobenzoyl chloride; triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 4h;
Inert atmosphere;
With
dmap;
In
tetrahydrofuran; toluene;
at 100 ℃;
Inert atmosphere;
DOI:10.1021/jo301122b
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / -78 °C / Inert atmosphere
2.1: pyridine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C / Inert atmosphere
4.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
4.2: 4 h
5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3.5 h / 20 °C
6.1: formic acid; water / tetrahydrofuran / 3 h / 0 °C
7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
7.2: 100 °C / Inert atmosphere
With
pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; ozone; triethylamine;
In
tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/jo301122b
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: pyridine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
2.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C / Inert atmosphere
3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.2: 4 h
4.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3.5 h / 20 °C
5.1: formic acid; water / tetrahydrofuran / 3 h / 0 °C
6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
6.2: 100 °C / Inert atmosphere
With
pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; water; ozone; triethylamine;
In
tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo301122b
