Technology Process of (2R,3R)-[(1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl]-3-hydroxy-4-[(2S,4S,6R)-2-(4-methoxyphenyl)-6-{[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl}-1,3-dioxan-4-yl]-2-methylbutanoate
There total 10 articles about (2R,3R)-[(1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl]-3-hydroxy-4-[(2S,4S,6R)-2-(4-methoxyphenyl)-6-{[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl}-1,3-dioxan-4-yl]-2-methylbutanoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate;
With
triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane;
In
dichloromethane;
at -78 ℃;
for 2h;
2-[(2R,4R,6R)-2-(4-methoxyphenyl)-6-{[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl}-1,3-dioxan-4-yl]acetaldehyde;
In
dichloromethane;
at -78 ℃;
for 2h;
optical yield given as %de;
diastereoselective reaction;
DOI:10.1021/jo2012658
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 0 - 20 °C
2.1: diisobutylaluminium hydride / hexanes; diethyl ether / 1.83 h / -78 °C
2.2: 3 h / 20 °C / Saturated solution
3.1: phenylborondichloride; (-)-sparteine / dichloromethane / 0.5 h / 0 - 20 °C
3.2: 16.17 h / 0 - 20 °C
3.3: 0.25 h / 20 °C / Cooling with ice
4.1: sodium tetrahydroborate / ethanol / 0 - 20 °C
4.2: 2.5 h
5.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C
7.1: pyridinium p-toluenesulfonate / toluene / 3 h / 90 °C
8.1: potassium carbonate; Dess-Martin periodane / dichloromethane / 15 h / 0 - 20 °C
9.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane / 2 h / -78 °C
9.2: 2 h / -78 °C
With
1H-imidazole; sodium tetrahydroborate; phenylborondichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; (-)-sparteine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane;
In
tetrahydrofuran; hexanes; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo2012658
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C
2.1: pyridinium p-toluenesulfonate / toluene / 3 h / 90 °C
3.1: potassium carbonate; Dess-Martin periodane / dichloromethane / 15 h / 0 - 20 °C
4.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane / 2 h / -78 °C
4.2: 2 h / -78 °C
With
tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane;
In
tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo2012658
![2-[(2R,4R,6R)-2-(4-methoxyphenyl)-6-{[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl}-1,3-dioxan-4-yl]acetaldehyde](/Databaselist/images/loading.webp)
