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

Autor:	Barbara Dmochowska, Rafał Ślusarz, Jarosław Chojnacki, Justyna Samaszko-Fiertek, Janusz Madaj
Jazyk:	angličtina
Rok vydání:	2020
Předmět:	sugar sulfonates quaternary ammonium salt methyl 2 3-O-isopropylidene-D-ribofuranoside heterocyclic amines X-ray crystallography Organic chemistry QD241-441
Zdroj:	Molecules, Vol 25, Iss 9, p 2161 (2020)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules25092161
Popis:	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.
Databáze:	Directory of Open Access Journals
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