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

• Main Authors: Barbara Dmochowska, Rafał Ślusarz, Jarosław Chojnacki, Justyna Samaszko-Fiertek, Janusz Madaj
• Format: Article
• Language: English
• Published: MDPI AG 2020-05-01
• Series: Molecules
• Subjects: sugar sulfonates; quaternary ammonium salt; methyl 2,3-<i>O</i>-isopropylidene-D-ribofuranoside; heterocyclic amines; X-ray crystallography
• Online Access: https://www.mdpi.com/1420-3049/25/9/2161
• ISSN: 1420-3049

The synthesis of <i>N</i>-((methyl 5-deoxy-2,3-<i>O</i>-isopropylidene-<i>β</i>-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-<i>O</i>-isopropylidene-5-<i>O</i>-tosyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-triflyl-<i>β</i>-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-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside and selected in silico interaction models are reported.