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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2020-05, Vol.25 (9), p.2161
• Main Authors: Dmochowska, Barbara, Ślusarz, Rafał, Chojnacki, Jarosław, Samaszko-Fiertek, Justyna, Madaj, Janusz
• Format: Article
• Language: English
• Subjects: Aliphatic amines; Amines; Ammonium; Ammonium salts; Computer Simulation; Crystallography, X-Ray; Heparan sulfate; heterocyclic amines; Interaction models; Magnetic Resonance Spectroscopy; methyl 2,3-O-isopropylidene-D-ribofuranoside; Models, Molecular; Molecular Structure; Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - chemistry; quaternary ammonium salt; Salts; Single crystals; sugar sulfonates; Sulfonates; Sulfonic Acids - chemistry; X-ray crystallography; X-ray diffraction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25092161

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.