Modification of arabinogalactan propargyl ethers by triazolyl functions

Polysaccharide arabinogalactan (AG) has been modified by triazolyl functions via the copper-catalyzed 1,3-dipolar addition of azides to propargyl ethers. A range of new AG triazolo derivatives bearing benzyl, 4-vinylbenzyl, 1-naphthylmethyl, (1-vinylimidazol-2-yl)methyl, (1-ethylimidazol-2-yl)methyl, (1-vinylbenzimidazol-2-yl)methyl, allyl, carboxymethyl (as Na-salt) substituents is prepared by “one-pot” approach from organic azides generated in situ and AG propargyl ethers. The latter (degree of substitution 2.0-2.2) are converted into 1,2,3-triazolo AGs in DMSO/water mixture in the presence of CuSO4·5H2O/sodium ascorbate/Et3N in 82-94% yields and with 60-100% conversion.