Technology Process of (R)-4-benzyl-3-((2R,3S,5R,6R)-6,9-bis((tert-butyldimethylsilyl)oxy)-3-hydroxy-5-methoxy-2,6-dimethylnonanoyl)oxazolidin-2-one
There total 9 articles about (R)-4-benzyl-3-((2R,3S,5R,6R)-6,9-bis((tert-butyldimethylsilyl)oxy)-3-hydroxy-5-methoxy-2,6-dimethylnonanoyl)oxazolidin-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
di-n-butylboryl trifluoromethanesulfonate; triethylamine;
In
dichloromethane;
at -78 - 0 ℃;
optical yield given as %de;
stereoselective reaction;
DOI:10.1021/jo201319b
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C
2.1: sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C
3.1: palladium 10% on activated carbon; hydrogen / ethanol
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
4.2: 2 h / -78 - 20 °C
5.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C
With
2,6-dimethylpyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; ethanol; dichloromethane;
4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Evans aldol reaction;
DOI:10.1021/jo201319b
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: propionic acid
2.1: lithium aluminium tetrahydride / diethyl ether
3.1: 1H-imidazole
4.1: AD-Mix-α
5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C
6.1: sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C
7.1: palladium 10% on activated carbon; hydrogen / ethanol
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
8.2: 2 h / -78 - 20 °C
9.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; AD-Mix-α; palladium 10% on activated carbon; hydrogen; sodium hydride; dimethyl sulfoxide; propionic acid; triethylamine;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
1.1: Johnson-Claisen orthoester rearrangement / 4.1: Sharpless dihydroxylation / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.1: Evans aldol reaction;
DOI:10.1021/jo201319b
