Technology Process of (3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-3,4-diol
There total 6 articles about (3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-3,4-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
hydrogen;
nickel;
In
ethanol;
at 20 ℃;
for 50h;
DOI:10.1021/jo9917700
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH2Cl2; decane / 16 h / -15 °C
2.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C
2.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C
3.1: HOAc (80percent) / 40 h / 20 °C
4.1: 1.6 g / pyridine / 4 h / 20 °C
5.1: H2 / Raney Ni / ethanol / 50 h / 20 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; hydrogen; tetra-(n-butyl)ammonium iodide;
nickel;
In
decane; ethanol; dichloromethane; dimethyl sulfoxide;
1.1: Sharpless asymmetric epoxidation / 2.1: Ring cleavage / 2.2: silylation / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Hydrogenation;
DOI:10.1021/jo9917700
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 92 percent / DIBAL / toluene; CH2Cl2 / 2 h / 20 °C
2.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH2Cl2; decane / 16 h / -15 °C
3.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C
3.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C
4.1: HOAc (80percent) / 40 h / 20 °C
5.1: 1.6 g / pyridine / 4 h / 20 °C
6.1: H2 / Raney Ni / ethanol / 50 h / 20 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; hydrogen; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride;
nickel;
In
decane; ethanol; dichloromethane; dimethyl sulfoxide; toluene;
1.1: Reduction / 2.1: Sharpless asymmetric epoxidation / 3.1: Ring cleavage / 3.2: silylation / 4.1: Ring cleavage / 5.1: Tosylation / 6.1: Hydrogenation;
DOI:10.1021/jo9917700