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Combined Ugi‐4CR/CuAAC Approach to Triazole‐Based Neoglycolipids
Author(s) -
PérezLabrada Karell,
Brouard Ignacio,
Méndez Inmaculada,
Pérez Carlos S.,
Gavín José A.,
Rivera Daniel G.
Publication year - 2014
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.201402117
Subject(s) - cycloaddition , chemistry , click chemistry , isomerization , combinatorial chemistry , triazole , azide , 1,3 dipolar cycloaddition , dendrimer , glycolipid , organic chemistry , stereochemistry , catalysis , biochemistry
Abstract New glycolipids that feature a carbohydrate/triazole/lipid hybrid architecture were readily produced by a combined multicomponent/click approach. The process comprises the use of the Ugi four‐component reaction to construct double‐lipidic scaffolds that have either alkyne or azide functionalities followed by conjugation to mono‐ and trisaccharides through a Cu I ‐catalyzed 1,3‐dipolar cycloaddition (click) process. The high chemical efficiency and feasibility of the overall procedure provides new opportunities for the rapid creation and biological screening of libraries of this unique class of Ugi/click glycolipids. Dynamic NMR experiments were performed to evaluate the free energy of activation related to the isomerization of the cis / trans amide bond in these compounds. This is the first time that such multicomponent and cycloaddition processes have been combined for the synthesis of glycolipids.