The quaternization reaction of 5-o-sulfonates of methyl 2,3-o-isopropylidene-β-D-ribofuranoside with selected heterocyclic and aliphatic amines

Article abstract of DOI:10.3390/molecules25092161

The synthesis of N-((methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside)-5-yl) ammoniumsalts 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 ormethyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranosidewere performed on amicro scale. High-resolution ¹H- and ¹³C-NMRspectraldata for all newcompoundswere recorded. Additionally, the single-crystalX-raydiffraction analysis formethyl 2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranoside and selected in silico interaction models are reported.