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

Barbara Dmochowska , Rafał Ślusarz , Jarosław Chojnacki , Justyna Samaszko-Fiertek , Janusz Madaj

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.
Author Barbara Dmochowska (FCh/DOCh/LCCh)
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
, Rafał Ślusarz (FCh/DOCh/LCCh)
Rafał Ślusarz,,
- Laboratory of Carbohydrate Chemistry
, Jarosław Chojnacki
Jarosław Chojnacki,,
-
, Justyna Samaszko-Fiertek (FCh/DOCh/LCCh)
Justyna Samaszko-Fiertek,,
- Laboratory of Carbohydrate Chemistry
, Janusz Madaj (FCh/DOCh/LCCh)
Janusz Madaj,,
- Laboratory of Carbohydrate Chemistry
Journal seriesMolecules, ISSN 1420-3049, (N/A 100 pkt)
Issue year2020
Vol25
No9
Pages1-12
Publication size in sheets0.55
Article number2161
Keywords in Polishczwartorzędowe sole amoniowe, 2,3-O-izopropylideno-D-rybofuranozyd metylu, heterocykliczne aminy
Keywords in Englishsugar sulfonates, quaternary ammonium salt, methyl 2,3-O-isopropylidene-D-ribofuranoside, heterocyclic amines, X-ray crystallography
ASJC Classification1605 Organic Chemistry
DOIDOI:10.3390/molecules25092161
URL https://doi.org/10.3390/molecules25092161
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa (CC-BY); with publication
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 13-07-2020, ArticleFromJournal
Publication indicators WoS Citations = 0.000; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 1.146; WoS Impact Factor: 2018 = 3.060 (2) - 2018=3.380 (5)
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