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The synthesis of <i>N</i>-((methyl 5-deoxy-2,3-<i>O</i>-isopropylidene-<i>β</i>-D-ribofuranoside)-5-yl)ammonium salts are presented. To determine the effect of the nucleophile type and outgoing group on the quaternization reaction, selected aliphatic and heterocyclic aromatic amines reacted with: methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-tosyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-triflyl-<i>β</i>-D-ribofuranoside were performed on a micro scale. High-resolution ¹H- and ¹³C-NMR spectral data for all new compounds were recorded. Additionally, the single-crystal X-ray diffraction analysis for methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside and selected in silico interaction models are reported.