Synthesis of Monomeric Methylene-Linked 1,2,3-Triazole Glycoconjugates from Allo- and Glucofuranoses

Chemistry of Heterocyclic Compounds 2015
Jeļena Grigorjeva, Jevgeņija Uzuleņa, Vitālijs Rjabovs, Māris Turks

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.

Keywords
diacetone glucose; diacetone allose; carbohydrate triazole conjugates; click chemistry; CuAAC
DOI
10.1007/s10593-015-1791-5
Hyperlink
https://link.springer.com/article/10.1007%2Fs10593-015-1791-5

Grigorjeva, J., Uzuleņa, J., Rjabovs, V., Turks, M. Synthesis of Monomeric Methylene-Linked 1,2,3-Triazole Glycoconjugates from Allo- and Glucofuranoses. Chemistry of Heterocyclic Compounds, 2015, Vol.51, No.10, pp.883-890. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-015-1791-5

Publication language
English (en)