通过 [3 + 2] 循环添加反应,对纳夫托 - 胺糖进行单立体选择合成
Likai Zhou1,2, Yaxin Cui1, Xiaoyan Huang1
1Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding, Hebei 071002, PR China.
The Journal of organic chemistry
|September 10, 2024
概括
研究人员使用 [3 + 2] 循环反应合成了新型纳夫托弗拉诺-胺基糖. 这种高效的方法提供了独特的选择性,并与多种氨酸衍生物一起工作,产生了有价值的化多循环 iminosugars.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 碳水化合物化学 碳水化合物化学
背景情况:
- 氨基糖是重要的碳水化合物模仿剂,具有多样化的生物活动.
- 开发高效的合成路径,以复杂的iminosugar支架仍然是有机合成的一个关键挑战.
研究的目的:
- 开发一种新且高效的合成战略,用于纳夫托 - - 氨基糖.
- 探索开发的反应的区域选择性和立体选择性.
- 用各种替代的anilines来证明该方法的适应性.
主要方法:
- 从2,3-O-异烯D-ribose托西酸盐 (1a),阿尼林 (2),和1,4-基 (3a) 中合成纳夫托弗拉诺-亚米诺糖 (4).
- 在室温 [3 + 2] 循环反应中利用了关键的离子/酶胺中间体.
- 通过使用电子捐赠和电子提取的替代anilines调查了反应范围.
主要成果:
- 实现了新型纳夫托弗拉诺-亚米诺糖的合成,产量中等至优异.
- 在循环化反应中表现出独特的区域选择性和立体选择性.
- 成功合成了化多循环伊米诺糖4并通过脱保护,环开放,脱水和消除将其转化为盐 (8).
结论:
- 开发的 [3 + 2] 循环化提供了一条有效的途径,以获得新型纳夫托福拉诺-亚米诺糖.
- 该方法具有多功能性,并且对氨酸成分上的各种替代剂具有耐受性.
- 意想不到的转化为盐突出了潜在的进一步合成应用.
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