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Syntheses of Bis ‐Triazole Linked Carbohydrate Based Macrocycles and Their Applications for Accelerating Copper Sulfate Mediated Click Reaction
Author(s) -
Chen Anji,
Samankumara Lalith P.,
Dodlapati Sanjeeva,
Wang Dan,
Adhikari Surya,
Wang Guijun
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801714
Subject(s) - chemistry , cycloaddition , click chemistry , azide , alkyne , triazole , combinatorial chemistry , anomer , 1,2,3 triazole , organic chemistry , stereochemistry , catalysis
Macrocyclic compounds play an important role in many research fields including drug discovery and development, bioorganic chemistry, and materials sciences. Carbohydrate‐based macrocycles are important compounds with unique structures and many potential applications. In this study, we have designed and synthesized a series of 1,2,3‐triazole linked and pyranose embedded macrocycles in short steps through the copper (I) catalyzed azide and alkyne cycloaddition reactions (CuAACs). Eight non‐symmetrical glucosamine based and bis‐triazole linked macrocycles have been synthesized starting from the readily available N‐ acetyl‐ d ‐glucosamine. These triazole‐linked glycomacrocycles showed remarkable reaction rate accelerations for CuSO 4 mediated azide and alkyne cycloaddition reactions in aqueous mixtures. Several azides including a sugar azide, which react sluggishly with alkynes, have been accelerated with the synthesized macrocycles. The benzoylated macrocycles with three methylene linkage at anomeric positions were the most effective among the eight macrocycles.