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

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

The synthesis of <i>N</i>-((methyl 5-deoxy-2,3-<i>O</i>-isopropylidene-<i>β</i>-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 heterocyc...

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Main Authors: Barbara Dmochowska, Rafał Ślusarz, Jarosław Chojnacki, Justyna Samaszko-Fiertek, Janusz Madaj
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Molecules
Subjects:
sugar sulfonates
quaternary ammonium salt
methyl 2,3-<i>O</i>-isopropylidene-D-ribofuranoside
heterocyclic amines
X-ray crystallography
Online Access:https://www.mdpi.com/1420-3049/25/9/2161
id doaj-289f6f948d0546309eb3d7b6caef3d03
record_format Article
spelling doaj-289f6f948d0546309eb3d7b6caef3d032020-11-25T02:04:44ZengMDPI AGMolecules1420-30492020-05-01252161216110.3390/molecules25092161The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic AminesBarbara Dmochowska0Rafał Ślusarz1Jarosław Chojnacki2Justyna Samaszko-Fiertek3Janusz Madaj4Carbohydrate Chemistry Group, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, PolandCarbohydrate Chemistry Group, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, PolandDepartment of Inorganic Chemistry, Technical University of Gdańsk, 80-233 Gdańsk, PolandCarbohydrate Chemistry Group, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, PolandCarbohydrate Chemistry Group, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, PolandThe synthesis of <i>N</i>-((methyl 5-deoxy-2,3-<i>O</i>-isopropylidene-<i>β</i>-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-<i>O</i>-isopropylidene-5-<i>O</i>-tosyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-triflyl-<i>β</i>-D-ribofuranoside were performed on a micro scale. High-resolution <sup>1</sup>H- and <sup>13</sup>C-NMR spectral data for all new compounds were recorded. Additionally, the single-crystal X-ray diffraction analysis for methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside and selected in silico interaction models are reported.https://www.mdpi.com/1420-3049/25/9/2161sugar sulfonatesquaternary ammonium saltmethyl 2,3-<i>O</i>-isopropylidene-D-ribofuranosideheterocyclic aminesX-ray crystallography
collection DOAJ
language English
format Article
sources DOAJ
author Barbara Dmochowska
Rafał Ślusarz
Jarosław Chojnacki
Justyna Samaszko-Fiertek
Janusz Madaj
spellingShingle Barbara Dmochowska
Rafał Ślusarz
Jarosław Chojnacki
Justyna Samaszko-Fiertek
Janusz Madaj
The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
Molecules
sugar sulfonates
quaternary ammonium salt
methyl 2,3-<i>O</i>-isopropylidene-D-ribofuranoside
heterocyclic amines
X-ray crystallography
author_facet Barbara Dmochowska
Rafał Ślusarz
Jarosław Chojnacki
Justyna Samaszko-Fiertek
Janusz Madaj
author_sort Barbara Dmochowska
title The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
title_short The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
title_full The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
title_fullStr The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
title_full_unstemmed The Quaternization Reaction of 5-<i>O</i>-Sulfonates of Methyl 2,3-<i>o</i>-Isopropylidene-<i>β</i>-D-Ribofuranoside With Selected Heterocyclic and Aliphatic Amines
title_sort quaternization reaction of 5-<i>o</i>-sulfonates of methyl 2,3-<i>o</i>-isopropylidene-<i>β</i>-d-ribofuranoside with selected heterocyclic and aliphatic amines
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-05-01
description The synthesis of <i>N</i>-((methyl 5-deoxy-2,3-<i>O</i>-isopropylidene-<i>β</i>-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-<i>O</i>-isopropylidene-5-<i>O</i>-tosyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside or methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-triflyl-<i>β</i>-D-ribofuranoside were performed on a micro scale. High-resolution <sup>1</sup>H- and <sup>13</sup>C-NMR spectral data for all new compounds were recorded. Additionally, the single-crystal X-ray diffraction analysis for methyl 2,3-<i>O</i>-isopropylidene-5-<i>O</i>-mesyl-<i>β</i>-D-ribofuranoside and selected in silico interaction models are reported.
topic sugar sulfonates
quaternary ammonium salt
methyl 2,3-<i>O</i>-isopropylidene-D-ribofuranoside
heterocyclic amines
X-ray crystallography
url https://www.mdpi.com/1420-3049/25/9/2161
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