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Synthesis of biologically important 4‐Phenyl‐ C ‐glycosyl‐1,2,3‐triazole derivatives by Cu(I)‐catalyzed azide–alkyne cycloaddition
Author(s) -
Ponnapalli Kalyana K.,
Kawade Sachin K.,
Adak Avijit K.,
Wu HsinRu,
Lin ChunCheng
Publication year - 2021
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000452
Subject(s) - chemistry , alkyne , cycloaddition , glycosyl , azide , yield (engineering) , catalysis , combinatorial chemistry , click chemistry , ligand (biochemistry) , substrate (aquarium) , triazole , organic chemistry , biochemistry , materials science , receptor , oceanography , metallurgy , geology
A new series of 4‐phenyl‐ C ‐glycosyl‐1,2,3‐triazoles were synthesized using Cu(I)‐ catalyzed azide–alkyne cycloaddition. The key step in the synthesis involved the coupling of unprotected glycosyl azides with substituted C ‐glycosylated phenyl acetylenes. Using o ‐phenylenediamine as a ligand, we could significantly reduce the reaction time, improve the product yield, and simplify the purification process. Broad substrate scope in terms of sugars was achieved.