A new benzhydryl-type protective groups for amides based on the concept of converting a stable protecting group into a labile one (safety-catch principle) are described. The p-substituted benzhydrylamine derivatives III(a, b), IV(a, b) are shown to be labile toward various acids but in their oxidized state - V(a, b), VI(a, b) exhibit the resistance to conditions commonly used for removal the Boc group. Independent removal of Boc or Fmoc groups, each in the presence of derivative VIa, is demonstrated by a synthesis of Pro-Leu-Gly-NH2. Some mechanistic aspects of deprotection reaction are discussed.
基于将稳定保护基转化为活性保护基的概念,描述了一种新的苯基二苯甲基型酰胺保护基。对于对位取代的苯基二苯甲胺衍生物III(a, b)、IV(a, b)显示出对各种酸具有活性,但在其氧化状态下 - V(a, b)、VI(a, b)表现出对常用于去除Boc基团的条件具有抗性。在衍生物VIa存在的情况下,演示了Boc或Fmoc基团的独立去除,通过合成Pro-Leu-Gly-NH2。讨论了一些去保护反应的机理方面。