Stereoselective Synthesis of Azobenzene-Based Glycomacrocycles

Synthesis Pub Date : 2024-06-11 DOI:10.1055/s-0043-1774911
Jinbiao Jiao, Juan Xie
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Abstract

Carbohydrate-based macrocyclic compounds are of particular interest because of their multifunctionality, their unique structural and physicochemical properties as well as their potential applications in chemistry, biology, and drug discovery. Introducing a molecular photoswitch into the skeleton of glycomacrocycles makes possible the reversible control of properties of the resulting photoswitchable glycomacrocycles by light illumination. Therefore, development of stereoselective synthesis of this class of glycomacrocycles is of great interest. Two new azobenzene-based glycomacrocycles have been synthesized through an intramolecular glycosylation approach. Excellent 1,2-cis stereoselectivity has been achieved for the mannosylation.

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偶氮苯基糖环的立体选择性合成
基于碳水化合物的大环化合物因其多功能性、独特的结构和物理化学特性以及在化学、生物学和药物发现领域的潜在应用而备受关注。将分子光开关引入糖环的骨架中,可以通过光照对所产生的光开关糖环的性质进行可逆控制。因此,开发该类糖环的立体选择性合成技术备受关注。我们通过分子内糖基化方法合成了两种新的偶氮苯基糖环。在甘露糖基化过程中实现了出色的 1,2-顺式立体选择性。
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