Technology Process of (R)-4-benzyl-3-((2S,6S,7R,8R,E)-8-(tert-butyldimethylsilyloxy)-7-methoxy-2,4,6-trimethyl-non-4-enoyl)oxazolidin-2-one
There total 10 articles about (R)-4-benzyl-3-((2S,6S,7R,8R,E)-8-(tert-butyldimethylsilyloxy)-7-methoxy-2,4,6-trimethyl-non-4-enoyl)oxazolidin-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3R)-3-propionyl-4-benzyloxazolidin-2-one;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
tert-butyl((2R,3R,4S,E)-7-iodo-3-methoxy-4,6-dimethylhept-5-en-2-yloxy)dimethylsilane;
In
tetrahydrofuran;
at -78 - -40 ℃;
for 2.83333h;
DOI:10.1021/ol102549a
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 12 h / 0 - 20 °C / Inert atmosphere
2.1: water / methanol / 48 h / 20 °C
3.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 23 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C
6.1: pyridine; ozone / methanol; dichloromethane / 0.58 h / -78 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / tetrahydrofuran / -78 - 20 °C
8.1: thionyl chloride / diethyl ether; hexane / -78 - 6 °C
9.1: sodium iodide / acetone / 12 h / 20 °C
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
10.2: 2.83 h / -78 - -40 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; ozone; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;
9.1: Finkelstein reaction;
DOI:10.1021/ol102549a
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C
2.1: pyridine; ozone / methanol; dichloromethane / 0.58 h / -78 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: hydrogenchloride; water / tetrahydrofuran / -78 - 20 °C
4.1: thionyl chloride / diethyl ether; hexane / -78 - 6 °C
5.1: sodium iodide / acetone / 12 h / 20 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
6.2: 2.83 h / -78 - -40 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; thionyl chloride; water; sodium hexamethyldisilazane; ozone; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;
5.1: Finkelstein reaction;
DOI:10.1021/ol102549a
