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

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 ¹H- and ¹³C-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.

X-ray crystallography; heterocyclic amines; methyl 2,3-O-isopropylidene-D-ribofuranoside; quaternary ammonium salt; sugar sulfonates.