Technology Process of (3aS,4R,6aR)-2-Oxo-4-(2-trimethylsilanyl-ethanesulfonylamino)-4,6a-dihydro-3aH-cyclopentaoxazole-3-carboxylic acid benzyl-methyl-amide
There total 14 articles about (3aS,4R,6aR)-2-Oxo-4-(2-trimethylsilanyl-ethanesulfonylamino)-4,6a-dihydro-3aH-cyclopentaoxazole-3-carboxylic acid benzyl-methyl-amide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-Trimethylsilanyl-ethanesulfonic acid ((3aS,4R,6aR)-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopentaoxazol-4-yl)-amide;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 0.25h;
benzyl(methyl)carbamic chloride;
In
tetrahydrofuran; hexane;
for 4h;
Heating;
With
1,4-diaza-bicyclo[2.2.2]octane;
In
tetrahydrofuran; hexane;
for 18h;
Heating;
DOI:10.1021/ol0490476
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: silver cyanide / benzene / 22 h / 75 °C
2.1: acetyl chloride / methanol / 2.17 h / 0 - 20 °C
2.2: 20 °C / pH 7
3.1: dmap; triethylamine / dichloromethane / 17 h / 0 - 20 °C
4.1: pyridine; dmap / 19.08 h / 20 °C
5.1: sodium iodide / acetone / 24 h / Heating / reflux
6.1: zinc / tetrahydrofuran; water / 3 h / Heating / reflux
7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 2.5 h / -20 °C
8.1: Hoveyda-Grubbs 2nd-generation catalyst / benzene / 14 h / Heating / reflux
9.1: potassium carbonate / methanol / 13 h / Heating / reflux
10.1: n-butyllithium / tetrahydrofuran; hexanes / 0.28 h / -78 °C
10.2: 4.33 h / -78 - 20 °C / Heating / reflux
10.3: 18 h / Heating / reflux
With
pyridine; dmap; n-butyllithium; silver cyanide; potassium hexamethylsilazane; potassium carbonate; triethylamine; acetyl chloride; sodium iodide; zinc;
Hoveyda-Grubbs 2nd-generation catalyst;
In
tetrahydrofuran; methanol; hexanes; dichloromethane; water; acetone; toluene; benzene;
6.1: Vasella reductive ring-opening / 7.1: Kocienski's modification of Julia reaction;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: silver cyanide / benzene / 22 h / 75 °C
2.1: acetyl chloride / methanol / 2.17 h / 0 - 20 °C
2.2: 20 °C / pH 7
3.1: dmap; triethylamine / dichloromethane / 17 h / 0 - 20 °C
4.1: pyridine; dmap / 19.08 h / 20 °C
5.1: sodium iodide / acetone / 24 h / Heating / reflux
6.1: zinc / tetrahydrofuran; water / 3 h / Heating / reflux
7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 2.5 h / -20 °C
8.1: Hoveyda-Grubbs 2nd-generation catalyst / benzene / 14 h / Heating / reflux
9.1: potassium carbonate / methanol / 13 h / Heating / reflux
10.1: n-butyllithium / tetrahydrofuran; hexanes / 0.28 h / -78 °C
10.2: 4.33 h / -78 - 20 °C / Heating / reflux
10.3: 18 h / Heating / reflux
With
pyridine; dmap; n-butyllithium; silver cyanide; potassium hexamethylsilazane; potassium carbonate; triethylamine; acetyl chloride; sodium iodide; zinc;
Hoveyda-Grubbs 2nd-generation catalyst;
In
tetrahydrofuran; methanol; hexanes; dichloromethane; water; acetone; toluene; benzene;
6.1: Vasella reductive ring-opening / 7.1: Kocienski's modification of Julia reaction;
