Stable Amide Activation of <i>N</i>-Acetylated Glycosamines for the Synthesis of Fused Polycyclic Glycomimetics
作者:Samaneh Zarei、Mélina Motard、Samy Cecioni
DOI:10.1021/acs.orglett.3c03803
日期:2024.1.12
underexplored target for chemoselective derivatization and generation of glycomimetic scaffolds. Through mild amide activation, we report that N-acetimidoyl heterocycles are stable in neutral or basic conditions yet are excellent leaving groups through acid catalysis. While this specific reactivity could prove broadly useful in amide activation strategies, stably activated N-acetylated sugars can also be diversified
碳水化合物的N-乙酰化是化学选择性衍生化和糖模拟支架生成的一个尚未充分探索的靶标。通过温和的酰胺活化,我们报告N-乙酰亚氨基杂环在中性或碱性条件下是稳定的,并且通过酸催化是优异的离去基团。虽然这种特定的反应性可能在酰胺活化策略中广泛有用,但也可以使用酰肼库使稳定活化的N-乙酰化糖多样化。我们优化了酸催化的一锅法序列,包括亲核置换、环脱水和分子内糖基化,最终产生与吗啉或哌嗪融合的吡喃糖苷。这种稳定激活后进行酸触发反应序列的策略例证了富含 3D 的融合糖模拟文库的有效组装。