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Combined Ugi-4CR/CuAAC approach to triazole-based neoglycolipids

AuthorsPérez-Labrada, Karell; Brouard, Ignacio ; Méndez, Inmaculada ; Perez, Carlos S.; Gavín, José A.
Click chemistry
Multicomponent reactions
Issue DateJun-2014
ChemPubSoc Europe
CitationEuropean Journal of Organic Chemistry 2014(17): 3671-3683 (2014)
AbstractNew 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 CuI‐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.
Publisher version (URL)https://doi.org/10.1002/ejoc.201402117
Identifiersdoi: 10.1002/ejoc.201402117
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IPNA) Artículos
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