DOI: https://doi.org/10.24959/ophcj.13.760

Synthesis of n-acetylglucosaminides dimers

O. Ye. Zemlyakov, V. M. Tsykalova, S. O. Zemlyakov, V. Ya. Chirva

Abstract


Glycosylation of aliphatic and aromatic α,ω-diols by the oxazoline method and by peracetylated α-D-glucosaminylchloride in the presence of zinc chloride and co-promoters (quaternary ammonium salts or trityl chloride) have been investigated. The highest yield of bis-glucosaminides in the conditions of oxazoline synthesis (the solvent is dichloroethane, the temperature of the reaction mixture is ~100°C, catalytic quantities of p-toluenesulfonic acid) has been observed for octane-1,8-diol. The products of monoglycosylation of butane-1,4-diol and dodecane-1,12-diol have been also obtained. The influence of the nature of a со-promoter has been studied on the model glycosylation reaction of octane-1,8-diol with peracetylated α-D-glucosaminylchloride in reflux dichloromethane (the ratio of glycosyl-acceptor : glycosyl-donor : zinc chloride : quaternary ammonium salt = 1 : 2,5 : 2,5 : 2,5). The best yields of dimeric glycoside have been obtained using tetrabutylammonium bromide. Increase of the amount of zinc chloride up to 1.5 equivalents in relation to the glycosyl donor has not led to significant changes of the reaction product yield. The yields of bis-glycosylation have been increased using peracetylated α-D-glucosaminylchloride as a glycosyl-donor for all aglycones. The corresponding mono- and bis-glucosaminides of 2,2’-(1,2-phenylenedioxy)diethanole have been synthesized by glycosylation in these conditions. The structure of the glycosides synthesized has been proven by 1H-NMR-spectroscopy.


Keywords


glucosaminides; glycoside synthesis; N-acetylglucosamine dimers

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