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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MDPI AG
2020-05-01
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| Series: | Molecules |
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| author | Barbara Dmochowska Rafał Ślusarz Jarosław Chojnacki Justyna Samaszko-Fiertek Janusz Madaj |
| author_facet | Barbara Dmochowska Rafał Ślusarz Jarosław Chojnacki Justyna Samaszko-Fiertek Janusz Madaj |
| author_sort | Barbara Dmochowska |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T20:01:04Z |
| format | Article |
| id | doaj.art-289f6f948d0546309eb3d7b6caef3d03 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:01:04Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-289f6f948d0546309eb3d7b6caef3d032023-11-19T23:31:48ZengMDPI AGMolecules1420-30492020-05-01259216110.3390/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 |
| 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 |
| 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_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_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_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 |
| 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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