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The synthesis of N -((methyl 5-deoxy-2,3- O -isopropylidene- β -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- O -isopropylidene-5- O -tosyl- β -D-ribofuranoside or methyl 2,3- O -isopropylidene-5- O -mesyl- β -D-ribofuranoside or methyl 2,3- O -isopropylidene-5- O -triflyl- β -D-ribofuranoside were performed on a micro scale. High-resolution 1 H- and 13 C-NMR spectral data for all new compounds were recorded. Additionally, the single-crystal X-ray diffraction analysis for methyl 2,3- O -isopropylidene-5- O -mesyl- β -D-ribofuranoside and selected in silico interaction models are reported.

The Quaternization Reaction of 5-O-Sulfonates of Methyl 2,3-o-Isopropylidene-β-D-Ribofuranoside with Selected Heterocyclic and Aliphatic Amines