Technology Process of (Z,2R,4R,6S)-2-phenyl-6-styryltetrahydro-2H-pyran-4-ol
There total 7 articles about (Z,2R,4R,6S)-2-phenyl-6-styryltetrahydro-2H-pyran-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere
1.2: 8 h / -78 - 20 °C / Inert atmosphere
2.1: silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Darkness; Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere
4.1: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere
5.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C / Inert atmosphere
8.2: 0.5 h / -78 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;
5.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation / 8.2: Wittig reaction;
DOI:10.1016/j.tetasy.2011.10.006
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Darkness; Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere
3.1: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere
4.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C / Inert atmosphere
7.2: 0.5 h / -78 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;
4.1: Mitsunobu reaction / 6.1: Dess-Martin oxidation / 7.2: Wittig reaction;
DOI:10.1016/j.tetasy.2011.10.006
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere
3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C / Inert atmosphere
6.2: 0.5 h / -78 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;
3.1: Mitsunobu reaction / 5.1: Dess-Martin oxidation / 6.2: Wittig reaction;
DOI:10.1016/j.tetasy.2011.10.006