Technology Process of (5S,6R,E)-tert-butyl 6-benzyloxy-13-(tert-butyldiphenylsilyloxy)-5-methyl-3,9-dioxotridec-7-enoate
There total 16 articles about (5S,6R,E)-tert-butyl 6-benzyloxy-13-(tert-butyldiphenylsilyloxy)-5-methyl-3,9-dioxotridec-7-enoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
6-benzyloxy-13-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-methyl-9-triethylsilanyloxy-tridec-7-enoic acid tert-butyl ester;
With
pyridinium p-toluenesulfonate;
In
ethanol;
at 20 ℃;
for 1.25h;
With
sodium hydrogencarbonate; Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
DOI:10.1002/anie.200502296
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C
2.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C
3.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C
4.1: 83 percent / Dibal-H / CH2Cl2 / 1.5 h / -78 - -50 °C
5.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C
6.1: PPTS / ethanol / 1.25 h / 20 °C
6.2: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C
With
1H-imidazole; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
1.1: Horner-Wadsworth-Emmons reaction / 6.2: Dess-Martin oxidation;
DOI:10.1002/anie.200502296
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: Et3N; DMAP / CH2Cl2 / 4 h / 20 °C
2.1: 4.23 g / dimethylsulfoxide / 24 h / 50 °C
3.1: O3 / methanol; CH2Cl2 / -78 °C
3.2: Me2S / methanol; CH2Cl2 / 3 h / 20 °C
4.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C
5.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C
6.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C
7.1: 83 percent / Dibal-H / CH2Cl2 / 1.5 h / -78 - -50 °C
8.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C
9.1: PPTS / ethanol / 1.25 h / 20 °C
9.2: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C
With
1H-imidazole; dmap; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
4.1: Horner-Wadsworth-Emmons reaction / 9.2: Dess-Martin oxidation;
DOI:10.1002/anie.200502296