反应剂控制的α-葡萄糖的立体选择合成
Liming Wang1, Herman S Overkleeft1, Gijsbert A van der Marel1
1Leiden Institute of Chemistry , Leiden University , Einsteinweg 55 , 2333 CC Leiden , The Netherlands.
Journal of the American Chemical Society
|March 20, 2018
概括
研究人员开发了一种立体选择性糖化方法来构建cis-glucosidic链接. 这种策略控制了特定的供体-接受体对的试剂激活,使复杂碳水化合物如Mycobacterium tuberculosis非糖化合物的有效合成成为可能.
科学领域:
- 碳水化合物化学
- 有机合成
- 葡萄糖生物学
背景情况:
- 由于捐赠体-接受体性质的变化,对糖链的立体选择性合成具有挑战性.
- 控制糖化结果需要精确调整试剂和保护组.
研究的目的:
- 开发一种针对cis-glucosidic链接的立体选择性合成的一般方法.
- 证明一种可适应不同酒精核友的策略 (初级与二级).
主要方法:
- 使用一种单一类型的甘酸供体 (化甘酸胺).
- 使用仅使用乙烯的保护组策略.
- 用特定的试剂组合激活了供体 (TMSOTf/DMF用于二次酒精,TMSI/Ph3PO用于初级酒精).
主要成果:
- 实现了完全立体选择的cis-glucosid链接.
- 根据受体反应性和试剂选择证明了差异激活.
- 成功地将该方法应用于Mycobacterium结核病非糖的模块化合成.
结论:
- 开发的策略可以精确控制糖化中的立体选择性.
- 这种方法为合成复杂的寡糖提供了一种多功能方法.
- 这些发现对推进碳水化合物合成和糖生物学研究具有重要意义.
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