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

Abstract

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.

Keywords

• sugar sulfonates
• quaternary ammonium salt
• methyl 2,3-<i>O</i>-isopropylidene-D-ribofuranoside
• heterocyclic amines
• X-ray crystallography