Technology Process of (S)-4-Benzyl-3-[(E)-(2S,3R,5S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoyl]-oxazolidin-2-one
There total 9 articles about (S)-4-Benzyl-3-[(E)-(2S,3R,5S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-oct-6-enoyl]-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 0 ℃;
for 0.25h;
(E)-(S)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enal;
In
dichloromethane;
at -78 ℃;
for 3h;
With
dihydrogen peroxide; sodium acetate;
In
methanol; dichloromethane; water;
at 0 ℃;
for 1.5h;
DOI:10.1021/jo034011x
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 84 percent / benzene / 48 h / 0 - 20 °C
2.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C
2.2: 78 percent / tetrahydrofuran / 0.08 h
3.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH2Cl2 / 20 h / -20 °C
3.2: 40 percent / FeSO4; citric acid / H2O; CH2Cl2
4.1: 76 percent / TfOH
5.1: DIBAL-H
6.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C
6.2: CH2Cl2 / 3 h / -78 °C
6.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH2Cl2; H2O / 1.5 h / 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine;
3 A molecular sieve;
In
tetrahydrofuran; dichloromethane; benzene;
1.1: Wittig olefination;
DOI:10.1021/jo034011x
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: O3 / CH2Cl2 / -78 °C
1.2: 100 percent / PPh3 / CH2Cl2 / -78 - 20 °C
2.1: 84 percent / benzene / 48 h / 0 - 20 °C
3.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C
3.2: 78 percent / tetrahydrofuran / 0.08 h
4.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH2Cl2 / 20 h / -20 °C
4.2: 40 percent / FeSO4; citric acid / H2O; CH2Cl2
5.1: 76 percent / TfOH
6.1: DIBAL-H
7.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C
7.2: CH2Cl2 / 3 h / -78 °C
7.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH2Cl2; H2O / 1.5 h / 0 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; ozone; diisopropylamine; N-ethyl-N,N-diisopropylamine;
3 A molecular sieve;
In
tetrahydrofuran; dichloromethane; benzene;
2.1: Wittig olefination;
DOI:10.1021/jo034011x
