Technology Process of [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester
There total 16 articles about [(1S)-1-[(4R)-4-benzyl-5-oxotetrahydrofuran-(2R)-2-yl]-3-(2,4,6-trimethoxybenzylcarbamoyl)propyl]carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
lithium bromide;
In
acetonitrile;
at 65 ℃;
DOI:10.1021/ol047879y
- Guidance literature:
-
Multi-step reaction with 7 steps
1: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C
2: Ac2O; Et3N / 1.25 h / Heating
3: 0.790 g / H2 / Pd/C / ethyl acetate; methanol / 4.25 h
4: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating
5: 78 percent / CrO3; H2SO4 / acetone / 1.5 h / -10 °C
6: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C
7: 95 percent / LiBr / acetonitrile / 65 °C
With
chromium(VI) oxide; dmap; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
5: Jones oxidation;
DOI:10.1021/ol047879y
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 1.44 g / H2 / Pd/C / ethyl acetate / 4 h
2: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C
3: 2.909 g / AcOH / toluene / 3 h / Heating
4: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C
5: Ac2O; Et3N / 1.25 h / Heating
6: 0.790 g / H2 / Pd/C / ethyl acetate; methanol / 4.25 h
7: 92 percent / DMAP / tetrahydrofuran / 21 h / Heating
8: 78 percent / CrO3; H2SO4 / acetone / 1.5 h / -10 °C
9: 92 percent / 1-HOBt; diisopropylethylamine; HBTU / dimethylformamide / 0 - 20 °C
10: 95 percent / LiBr / acetonitrile / 65 °C
With
chromium(VI) oxide; dmap; sulfuric acid; hydrogen; acetic anhydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
8: Jones oxidation;
DOI:10.1021/ol047879y
