Technology Process of (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane
There total 3 articles about (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
potassium cyanide; (2S,3R,4R)-2,3-epoxy-4,5-(cyclohexylidenedioxy)pentan-1-ol;
With
titanium(IV) isopropylate; tetra-(n-butyl)ammonium iodide;
In
dimethyl sulfoxide;
at 20 ℃;
for 60h;
tert-butylchlorodiphenylsilane;
With
1H-imidazole;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 2h;
Further stages.;
DOI:10.1021/jo9917700
- Guidance literature:
-
Multi-step reaction with 2 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
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide;
In
decane; dichloromethane; dimethyl sulfoxide;
1.1: Sharpless asymmetric epoxidation / 2.1: Ring cleavage / 2.2: silylation;
DOI:10.1021/jo9917700
- Guidance literature:
-
Multi-step reaction with 3 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
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride;
In
decane; dichloromethane; dimethyl sulfoxide; toluene;
1.1: Reduction / 2.1: Sharpless asymmetric epoxidation / 3.1: Ring cleavage / 3.2: silylation;
DOI:10.1021/jo9917700
