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SYNTHESIS OF MONOMERIC METHYLENE-LINKED 1,2,3-TRIAZOLE GLYCOCONJUGATES FROM ALLO- AND GLUCOFURANOSES

Jeļena Grigorjeva, Jevgeņija Uzuleņa, Vitālijs Rjabovs, Māris Turks
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Abstract


Carbohydrate–triazole conjugates proved themselves as valuable enzyme activity-modifying agents. Recent exploration of nontrivial conjugates in which the bonding is formed not at the glycosidic or terminal carbons of the carbohydrates, but at C-3 position showed a potential of this type of structures as the ligands for various glycosidases and galectins. Here, we report synthesis of protected monomeric 3-C-(triazolylmethyl)-substituted gluco- and alloconjugates. Diastereomeric azides are synthesized from common intermediate, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-oxo-α-D-allofuranose, and used in Cu-catalyzed azide–alkyne cycloaddition (CuAAC) reactions with commercial alkynes. The yields of the cycloaddition reactions are good to excellent under different catalytic conditions.

How to Cite
Grigorjeva, J.; Uzuleņa, J.; Rjabovs, V.; Turks, M. Chem. Heterocycl. Compd. 2015, 51, 883. [Khim. Geterotsikl. Soedin. 2015, 51, 883.]

For this article in the English edition see DOI 10.1007/s10593-015-1791-5


Keywords


diacetone glucose; diacetone allose; carbohydrate triazole conjugates; click chemistry; CuAAC

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