基于糖烯的碳苷合成方法研究进展

Advances in the Synthesis of C-Glycosides from Glycals

碳苷是一类具有多种生物活性的糖类天然产物,其独特的C—C糖苷键构筑是糖化学研究中的热点和难点.通过双键官能团构建新的C—C键是有机化学中的常用策略.随着烯化学的飞速发展,含1,2-位双键的糖烯供体在碳苷合成中也取得了显著进步.从Ferrier I型碳苷化反应、Heck偶联型碳苷化反应、1-取代糖烯的过渡金属催化偶联碳苷化反应、2-取代糖烯的Michael加成型和自由基加成型碳苷化反应等方面,总结近年来基于糖烯的碳苷合成方法.

C-Glycosides are a class of carbohydrates with a variety of biological activities,and the construction of their unique C-C glycosidic bond is a hot and challenging topic in carbohydrate chemistry.The formation of new C-C bond from carbon-carbon double bond is a common strategy in organic chemistry.With the rapid development of ene-chemistry,great progress in the synthesis of C-glycosides from glycal donors containing 1,2-double bond has been made.In this review,the methods for the synthesis of C-glycosides based on glycals are summarized,including Ferrier I-type C-glycosylation,Heck-type C-glycosylation,C-glycosylation of 1-substituted glycals using transition metal-catalyzed coupling reaction,Michael-type C-glycosylation of 2-substituted glycals,and radical addition type C-glycosylation of glycals.