The Quaternization Reaction of 5-O-Sulfonates of Methyl 23-o-Isopropylidene-β-D-Ribofuranoside with Selected Heterocyclic and Aliphatic Amines

摘要

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