| 刘洋洋,叶鑫,马圣洲,等.2-(甲氨基)乙基糖苷的高效合成[J].中国海洋药物,2022,41(3):10-16. |
| 2-(甲氨基)乙基糖苷的高效合成 |
| Efficient synthesis of N-methylethyl glycosides |
| 投稿时间：2021-05-13 修订日期：2021-05-19 |
| DOI： |
| 中文关键词: N-甲基乙基糖苷 糖基化 高效 合成 |
| English Keywords:N-Methylethyl glycoside glycosylation efficient synthesis |
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| 中文摘要: |
| 目的 通过化学合成的手段进行N-甲基乙基糖苷的高效合成。方法 以单糖为原料,首先制备苯甲酰化的三氯乙酰亚胺酯糖基供体,然后与苄氧基羰基(Cbz)保护的2-N-甲氨基乙醇进行糖苷化反应,最后依次脱除苯甲酰基和苄氧羰基保护基团,得到N-甲基乙基糖苷目标化合物。结果 基于此策略合成了葡萄糖、半乳糖、木糖、岩藻糖和阿拉伯糖的N-甲基乙基糖苷,6步总收率为60%~74%；结构均经1H NMR,13C NMR和HR-MS(ESI)表征。结论 本文建立的合成N-甲基乙基糖苷的方法具有简单高效、立体选择性好和适用性广的特点。 |
| English Summary: |
| Objective Efficient synthesis of N-methylethyl glycosides by means of chemical synthesis. Methods Using monosaccharides as raw materials, the benzoylated trichloroacetimidate glycosyl donors were firstly prepared, followed by glycosylation reaction with benzyloxycarbonyl (Cbz)-protected 2-N-methylaminoethanol, and finally the benzoyl and benzyloxycarbonyl protecting groups were sequentially removed to obtain the target compounds of N-methylethyl glycosides. Results Based on this strategy, N-methylethyl glycosides of glucose, galactose , xylose, fucose and arabinose were synthesized with a total yield of 60%~74% in 6 steps. The structures were characterized by 1 H NMR, 13C NMR and HR-MS (ESI). Conclusion The established method for the synthesis of N-methylethyl glycosides was simple and efficient, with good stereoselectivity and wide applicability. |
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