Technology Process of (2S,3S,5R,6R)-5-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2-methyloct-7-ene-1-ol
There total 5 articles about (2S,3S,5R,6R)-5-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2-methyloct-7-ene-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
lithium borohydride;
In
methanol; diethyl ether;
at 0 ℃;
for 12h;
Inert atmosphere;
DOI:10.1021/ol5011278
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
3.2: 12 h / -78 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere
5.1: lithium borohydride / methanol; diethyl ether / 12 h / 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; water; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
methanol; diethyl ether; dichloromethane;
2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Aldol Addition / 3.2: |Aldol Addition;
DOI:10.1021/ol5011278
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
4.2: 12 h / -78 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere
6.1: lithium borohydride / methanol; diethyl ether / 12 h / 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 4.1: |Aldol Addition / 4.2: |Aldol Addition;
DOI:10.1021/ol5011278
![(R)-4-benzyl-3-[(2R,3S,5R,6R)-5-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2-methyloct-7-enoyl]oxazolidin-2-one](/Databaselist/images/loading.webp)
