Technology Process of [(2R,4R,6S)-6-((2RS,6R)-7-benzyloxy-2-hydroxy-4-oxo-6-triethylsilanyloxyheptyl)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]acetic acid tert-butyl ester
There total 11 articles about [(2R,4R,6S)-6-((2RS,6R)-7-benzyloxy-2-hydroxy-4-oxo-6-triethylsilanyloxyheptyl)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]acetic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h
1.2: tetrahydrofuran; hexane / 0.5 h / Heating
2.1: 87.3 g / Et2BOMe; NaBH4 / tetrahydrofuran; methanol
3.1: PPTS / CH2Cl2 / 2.5 h / Heating
4.1: 33.0 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h
5.1: Et3N / CH2Cl2 / 4.25 h / 20 °C
6.1: NaI; NaHCO3; Na2SO3 / butan-2-one / 16 h / Heating
7.1: Li2CuCl4 / tetrahydrofuran
8.1: O3 / CH2Cl2; methanol / 1 h
8.2: 33.6 g / tributylphosphine / CH2Cl2; methanol / 0.17 h
9.1: LDA / tetrahydrofuran; hexane / 1 h
9.2: 50.8 g / tetrahydrofuran; hexane / 0.25 h
With
sodium tetrahydroborate; dilithium tetrachlorocuprate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ozone; triethylamine; sodium iodide; sodium sulfite; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; butanone;
1.2: Claisen condensation;
DOI:10.1021/ja030316h
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: imidazole / dimethylformamide / 0 - 20 °C
2.1: O3; NaHCO3 / methanol; CH2Cl2
2.2: 51.1 g / dimethyl sulfide / methanol; CH2Cl2 / 12 h
3.1: LDA / tetrahydrofuran; hexane / 1 h
3.2: 50.8 g / tetrahydrofuran; hexane / 0.25 h
With
1H-imidazole; sodium hydrogencarbonate; ozone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja030316h
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: Et3N / CH2Cl2 / 4.25 h / 20 °C
2.1: NaI; NaHCO3; Na2SO3 / butan-2-one / 16 h / Heating
3.1: Li2CuCl4 / tetrahydrofuran
4.1: O3 / CH2Cl2; methanol / 1 h
4.2: 33.6 g / tributylphosphine / CH2Cl2; methanol / 0.17 h
5.1: LDA / tetrahydrofuran; hexane / 1 h
5.2: 50.8 g / tetrahydrofuran; hexane / 0.25 h
With
dilithium tetrachlorocuprate; sodium hydrogencarbonate; ozone; triethylamine; sodium iodide; sodium sulfite; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; butanone;
DOI:10.1021/ja030316h