Technology Process of 2-(trimethylsilyl)ethyl 2-hydroxy-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate
There total 14 articles about 2-(trimethylsilyl)ethyl 2-hydroxy-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-(Trimethylsilyl)ethanol;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at 0 ℃;
for 0.5h;
Inert atmosphere;
2,2-dimethyl-5-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)-4H-benzo[d][1,3]dioxin-4-one;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 3.5h;
Inert atmosphere;
DOI:10.1021/ol201863b
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 2 h / -78 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h
3.1: sodium iodide / acetone / 12 h / Reflux; Inert atmosphere
4.1: N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
5.1: scandium tris(trifluoromethanesulfonate) / methanol / 24 h / 20 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C / Inert atmosphere
7.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.2: 3.5 h / 0 - 20 °C / Inert atmosphere
With
oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; sodium iodide; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
6.1: Swern oxidation / 7.1: Julia-Kocienski olefination;
DOI:10.1021/ol201863b
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere
2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; benzene / 2 h / -78 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h
4.1: sodium iodide / acetone / 12 h / Reflux; Inert atmosphere
5.1: N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
6.1: scandium tris(trifluoromethanesulfonate) / methanol / 24 h / 20 °C / Inert atmosphere
7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 °C / Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
9.2: 3.5 h / 0 - 20 °C / Inert atmosphere
With
oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium iodide; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
7.1: Swern oxidation / 8.1: Julia-Kocienski olefination;
DOI:10.1021/ol201863b
