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4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole
The title compound, C(18)H(27)N(3)O(7), was synthesized by Cu(I)-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyranose N-glycoside, thus confirming...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977263/ https://www.ncbi.nlm.nih.gov/pubmed/21583666 http://dx.doi.org/10.1107/S1600536809028700 |
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author | Alhassan, Abdul-Basit Norris, Peter Zeller, Matthias |
author_facet | Alhassan, Abdul-Basit Norris, Peter Zeller, Matthias |
author_sort | Alhassan, Abdul-Basit |
collection | PubMed |
description | The title compound, C(18)H(27)N(3)O(7), was synthesized by Cu(I)-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyranose N-glycoside, thus confirming the retention of stereochemistry during heterocycle formation with the N-glycosyl triazole group occupying the equatorial position at the anomeric C atom. The structure exhibits two crystallographically independent molecules (A and B) with essentially identical conformations with a weighted r.m.s. deviation of only 0.09 Å. The molecules are arranged in layers with hydrophobic and more polar sections built from the butyl triazole units on the one hand and the more polar moieties dominated by the carbohydrate units on the other. Within the polar layers, intermolecular interactions are dominated by a three-dimensional network of weak C—H⋯O hydrogen bonds with the acetyl keto O atoms as the hydrogen-bond acceptors. The triazole units interact with each other via C—H⋯N hydrogen bonds which connect the molecules into two infinite chains of molecules made up of either A molecules or B molecules that stretch parallel to each other along [100]. Between the butyl groups no directional interactions are observed. |
format | Text |
id | pubmed-2977263 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29772632010-12-30 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole Alhassan, Abdul-Basit Norris, Peter Zeller, Matthias Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(27)N(3)O(7), was synthesized by Cu(I)-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyranose N-glycoside, thus confirming the retention of stereochemistry during heterocycle formation with the N-glycosyl triazole group occupying the equatorial position at the anomeric C atom. The structure exhibits two crystallographically independent molecules (A and B) with essentially identical conformations with a weighted r.m.s. deviation of only 0.09 Å. The molecules are arranged in layers with hydrophobic and more polar sections built from the butyl triazole units on the one hand and the more polar moieties dominated by the carbohydrate units on the other. Within the polar layers, intermolecular interactions are dominated by a three-dimensional network of weak C—H⋯O hydrogen bonds with the acetyl keto O atoms as the hydrogen-bond acceptors. The triazole units interact with each other via C—H⋯N hydrogen bonds which connect the molecules into two infinite chains of molecules made up of either A molecules or B molecules that stretch parallel to each other along [100]. Between the butyl groups no directional interactions are observed. International Union of Crystallography 2009-07-25 /pmc/articles/PMC2977263/ /pubmed/21583666 http://dx.doi.org/10.1107/S1600536809028700 Text en © Alhassan et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Alhassan, Abdul-Basit Norris, Peter Zeller, Matthias 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title | 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title_full | 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title_fullStr | 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title_full_unstemmed | 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title_short | 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fucopyranosyl)-1H-1,2,3-triazole |
title_sort | 4-butyl-1-(2,3,4-tri-o-acetyl-β-l-fucopyranosyl)-1h-1,2,3-triazole |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977263/ https://www.ncbi.nlm.nih.gov/pubmed/21583666 http://dx.doi.org/10.1107/S1600536809028700 |
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