Modification of arabinogalactan propargyl ethers by triazolyl functions

作者：Grischenko Lyudmila A; Parshina Lidiya N; Larina Lyudmila I; Novikova Lyubov N; Trofimov Boris A^*

来源：Carbohydrate Polymers, 2015, 115: 294-304.

DOI：10.1016/j.carbpol.2014.08.050

• Arabinogalactan functionalization
• Biopolymers
• 1,3-Dipolar cycloaddition
• Sodium azide
• Organyl halides

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 "onepot" 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 center dot 5H(2)O/sodium ascorbate/Et3N in 82-94% yields and with 60-100% conversion.

• 出版日期2015-1-22