Technology Process of (4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-[(1S)-1,2-dihydroxyethyl]oxazolidin-2-one
There total 6 articles about (4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-[(1S)-1,2-dihydroxyethyl]oxazolidin-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate;
With
diisobutylaluminium hydride;
In
dichloromethane; toluene;
at -78 ℃;
for 1h;
Inert atmosphere;
With
Glauber's salt;
In
dichloromethane; acetone; toluene;
at 0 - 20 ℃;
for 1.5h;
DOI:10.1016/j.tetasy.2012.04.012
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere
4.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere
5.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere
6.2: 1.5 h / 0 - 20 °C
With
pyridine; dmap; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; benzoic acid; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
5.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere
4.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere
5.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere
6.2: 1.5 h / 0 - 20 °C
With
pyridine; dmap; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; benzoic acid; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
5.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012
![ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate](/Databaselist/images/loading.webp)
