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Synthesis of monomeric methylene-linked 1,2,3-triazole glycoconjugates from allo- and glucofuranoses

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This work was supported by the Latvian Council of Science (grant No. 10.0030). The authors thank JSC ''Olainfarm'' for kind donation of diacetone-D-glucose. JSC ''Grindeks'' is acknowledged for kind donation of organic solvents.

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Correspondence to Vitālijs Rjabovs.

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Pablished in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 883–890

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Grigorjeva, J., Uzuleņa, J., Rjabovs, V. et al. Synthesis of monomeric methylene-linked 1,2,3-triazole glycoconjugates from allo- and glucofuranoses. Chem Heterocycl Comp 51, 883–890 (2015). https://doi.org/10.1007/s10593-015-1791-5

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