An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars
Abstract
:1. Introduction
2. Results and Discussion
2.1. The Unsuccessful N-alkylation Strategy
2.2. The Preparation of Diethyl Dithioacetal
Entry | Additives | Eq. | Solvent | Tem. (°C) | Yield a (%) |
---|---|---|---|---|---|
1 | TMSCl | 0.2 | CHCl3 | RT | - |
2 | BF3·Et2O | 0.2 | CHCl3 | RT | - |
3 | AcCl | 0.2 | CH2Cl2 | RT | - |
5 | conc. HCl | excess | MeOH | RT | - |
6 | HCl (g) | excess | Dioxane | RT | 56 |
7 | BDMS | 0.2 | CH3CN | 0- RT | trace |
8 | BDMS | 0.2 | CH2Cl2 | 0- RT | trace |
9 | BDMS | 0.2 | EtSH | RT | 84 b |
2.3. Completion of the Synthesis
3. Experimental
3.1. General Methods
3.2. Synthesis
4. Conclusions
Supplementary Materials
Acknowledgments
Conflicts of Interest
References
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Zhao, H.; Zhao, W.-B.; Zhu, J.-S.; Jia, Y.-M.; Yu, C.-Y. An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars. Molecules 2013, 18, 6021-6034. https://doi.org/10.3390/molecules18056021
Zhao H, Zhao W-B, Zhu J-S, Jia Y-M, Yu C-Y. An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars. Molecules. 2013; 18(5):6021-6034. https://doi.org/10.3390/molecules18056021
Chicago/Turabian StyleZhao, Hui, Wen-Bo Zhao, Jian-She Zhu, Yue-Mei Jia, and Chu-Yi Yu. 2013. "An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones: Precursors of Piperidine Iminosugars" Molecules 18, no. 5: 6021-6034. https://doi.org/10.3390/molecules18056021