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

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

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 microscale. High-resolution 1H- and13C-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

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Category:
Articles
Type:
artykuły w czasopismach
Published in:
MOLECULES no. 25, pages 2161 - 2173,
ISSN: 1420-3049
Language:
English
Publication year:
2020
Bibliographic description:
Dmochowska B., Ślusarz R., Chojnacki J., Samaszko-Fiertek J., Madaj J.: The Quaternization Reaction of 5-O-Sulfonates of Methyl 2,3-o-Isopropylidene-β-D-Ribofuranoside with Selected Heterocyclic and Aliphatic Amines// MOLECULES -Vol. 25,iss. 9 (2020), s.2161-2173
DOI:
Digital Object Identifier (open in new tab) 10.3390/molecules25092161
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