SYNTHESIS OF NOVEL 3-[(1-GLYCOSYL-1<i>H</i>-1,2,3-TRIAZOL-4-YL)- METHYLAMINO]KET-2-EN-1-ONES

Abstract

Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine derivatives and 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose or 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, followed by deprotection of the resulting tri-O-benzoyl- or tetra-O-acetyl-1-β-D-glycosyltriazoles in good yields. The precursor propargylamine derivatives were synthesized by Sonogashira reaction of substituted acetylenes and benzoyl chloride followed by Michael-type addition of propargylamine to the resulting substituted alkynes in good yields. The precursor azido sugars, 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose and 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, were synthesized by azidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and β-D-glucopyranose pentacetate, respectively, with azidotrimethylsilane in the presence of tin(IV) chloride. All products were unambiguously characterized on the basis of the spectral data analysis.