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

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- -isopropylid...

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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
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container_title Molecules (Basel, Switzerland)
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creator Dmochowska, Barbara
Ślusarz, Rafał
Chojnacki, Jarosław
Samaszko-Fiertek, Justyna
Madaj, Janusz
description 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.
doi_str_mv 10.3390/molecules25092161
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source PubMed (Medline); Publicly Available Content Database (Proquest) (PQ_SDU_P3)
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
title The Quaternization Reaction of 5- O -Sulfonates of Methyl 2,3- o -Isopropylidene- β -D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
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