Technology Process of (2R,5S,E)-1-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methyl-9-((tetrahydro-2H-pyran-2-yl)oxy)non-7-en-4-one
There total 11 articles about (2R,5S,E)-1-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methyl-9-((tetrahydro-2H-pyran-2-yl)oxy)non-7-en-4-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane;
With
tert.-butyl lithium;
In
diethyl ether; pentane;
at -78 ℃;
for 0.25h;
(2S,E)-N-methoxy-2-((4-methoxybenzyl)oxy)-N-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-enamide;
In
tetrahydrofuran; diethyl ether; pentane;
at -78 ℃;
DOI:10.1039/c0ob01253j
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / ethanol; water; dimethyl sulfoxide / 0.5 h / 20 °C
2.1: acetic acid; zinc / ethanol / 2 h / 20 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C
4.1: camphor-10-sulfonic acid / dichloromethane / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
7.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 0.5 h / 0 °C
8.1: 1,1'-carbonyldiimidazole / dichloromethane / 0 °C
9.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C
9.2: -78 °C
With
1H-imidazole; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; zinc;
In
tetrahydrofuran; 2-methyl-but-2-ene; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;
6.1: Parikh-Doering oxidation;
DOI:10.1039/c0ob01253j
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: acetic acid; zinc / ethanol / 2 h / 20 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C
3.1: camphor-10-sulfonic acid / dichloromethane / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
5.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
6.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 0.5 h / 0 °C
7.1: 1,1'-carbonyldiimidazole / dichloromethane / 0 °C
8.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C
8.2: -78 °C
With
1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; zinc;
In
tetrahydrofuran; 2-methyl-but-2-ene; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;
5.1: Parikh-Doering oxidation;
DOI:10.1039/c0ob01253j