Technology Process of (4S)-4-benzyl-3-[(2S,3R,4R,6Z)-3-hydroxy-8-[(4-methoxyphenyl)methoxy]-2,4-dimethyloct-6-enoyl]-1,3-oxazolidin-2-one
There total 4 articles about (4S)-4-benzyl-3-[(2S,3R,4R,6Z)-3-hydroxy-8-[(4-methoxyphenyl)methoxy]-2,4-dimethyloct-6-enoyl]-1,3-oxazolidin-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(S)-4-benzyl-3-propionyl-2-oxazolidinone;
With
di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at -78 - 20 ℃;
for 1h;
Inert atmosphere;
(R,Z)-6-((4-methoxybenzyl)oxy)-2-methylhex-4-enal;
In
dichloromethane;
at -78 ℃;
for 3h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/jo300225z
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: quinoline; hydrogen / ethyl acetate / 2 h
2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
3.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
3.2: 3 h / -78 °C / Inert atmosphere
With
quinoline; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
dichloromethane; ethyl acetate;
2.1: Swern oxidation / 3.1: Evans aldol reaction / 3.2: Evans aldol reaction;
DOI:10.1021/jo300225z
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / methanol / 2 h / 0 - 20 °C / Inert atmosphere
2.1: quinoline; hydrogen / ethyl acetate / 2 h
3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere
4.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
4.2: 3 h / -78 °C / Inert atmosphere
With
quinoline; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
methanol; dichloromethane; ethyl acetate;
3.1: Swern oxidation / 4.1: Evans aldol reaction / 4.2: Evans aldol reaction;
DOI:10.1021/jo300225z
