Technology Process of (4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one
There total 1 articles about (4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
C27H38O5Si;
With
N,N,N,N,-tetramethylethylenediamine;
In
dichloromethane;
at 60 ℃;
for 1h;
Molecular sieve;
With
pyridinium chlorochromate;
In
dichloromethane;
at 20 ℃;
for 1h;
DOI:10.3987/COM-10-S(E)27
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: cerium(III) chloride heptahydrate / dichloromethane; methanol / 1 h / 20 °C
1.2: 0.5 h / -78 °C
2.1: 2-hydroxynitrobenzene / 52 h / 140 °C / Sealed tube; Inert atmosphere
3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 0 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol / 1 h / 20 °C
4.2: 1 h / 20 °C
5.1: dmap; 1,1'-Thiocarbonyldiimidazole / 1,2-dichloro-benzene / 6 h / Reflux
6.1: lithium hydroxide monohydrate / ethanol; water / 20 h / 20 °C
7.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2.5 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux
With
dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium hydroxide monohydrate; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; 2-hydroxynitrobenzene;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene;
7.1: |Pictet-Spengler Synthesis;
DOI:10.3987/COM-10-S(E)27
- Guidance literature:
-
(4R,6S)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one;
With
cerium(III) chloride heptahydrate;
In
methanol; dichloromethane;
at 20 ℃;
for 1h;
With
sodium tetrahydroborate;
In
methanol; dichloromethane;
at -78 ℃;
for 0.5h;
DOI:10.3987/COM-10-S(E)27
