Chapter 11 - Synthesis of carbohydrate-containing macrocycles

Abstract

Carbohydrate-based macrocyclic compounds have gained an intense interest in the scientific community due to their unique properties, drug likeness, ion complexation capacity, and as ligands for catalysis. In this chapter, the most recent studies on carbohydrate-embedded macrocycles will be reviewed, including publications from 2011 to 2021. The review will discuss sugar-containing macrocycles with an emphasis on their synthetic strategies and briefly discuss their applications when appropriate. Since there are numerous macrocycles with sugar attached at the periphery of the macrocycle, this chapter will only focus on sugar-embedded macrocycles, in which the carbohydrates are part of the macrocyclic ring systems. The main topics covered include naturally occurring glycomacrocycles and synthetic sugar-based macrocycles. Among the nonnatural glycomacrocycles, several topics will be included: sugar-based crown ether and azacrown ethers, sucrose-based macrocycles, heterocycle-containing sugar-embedded macrocycles, synthesis of macrocycles containing specific functional groups, and lastly miscellaneous glycomacrocycles. The method for the synthesis, especially the macrocyclization methods used are discussed in detail for each representative class of macrocycles.