title: Modification of arabinogalactan propargyl ethers by triazolyl functions.
abstract: 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.
authors.affiliation: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
authors.forename: Lyudmila A
authors.initials: LA
authors.lastname: Grischenko
authors.affiliation: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
authors.forename: Lidiya N
authors.initials: LN
authors.lastname: Parshina
authors.affiliation: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
authors.forename: Lyudmila I
authors.initials: LI
authors.lastname: Larina
authors.affiliation: Irkutsk State Agricultural Academy, Molodezhny Settlement, 664038 Irkutsk, Russia.
authors.forename: Lyubov N
authors.initials: LN
authors.lastname: Novikova
authors.affiliation: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. Electronic address: boris_trofimov@irioch.irk.ru.
authors.forename: Boris A
authors.initials: BA
authors.lastname: Trofimov
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D005685:Galactans / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D004987:Ethers; D005685:Galactans; D014230:Triazoles; C531209:propargyl ether; C005653:arabinogalactan
keywords: 1,3-Dipolar cycloaddition; Arabinogalactan functionalization; Biopolymers; Organyl halides; Sodium azide