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Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside
In the title compound, C(30)H(31)NO(6)S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thioethyl group has the exo-anomeric co...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011472/ https://www.ncbi.nlm.nih.gov/pubmed/21589536 http://dx.doi.org/10.1107/S1600536810047069 |
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author | Hamark, Christoffer Landström, Jens Eriksson, Lars Widmalm, Göran |
author_facet | Hamark, Christoffer Landström, Jens Eriksson, Lars Widmalm, Göran |
author_sort | Hamark, Christoffer |
collection | PubMed |
description | In the title compound, C(30)H(31)NO(6)S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thioethyl group has the exo-anomeric conformation. The hydroxy group forms an intermolecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close π–π contacts with centroid–centroid distances less than 4.0 Å, all with dihedral angles between the interacting π systems of only ≃ 8°, supporting energetically favourable stacking interactions. |
format | Text |
id | pubmed-3011472 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30114722010-12-30 Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside Hamark, Christoffer Landström, Jens Eriksson, Lars Widmalm, Göran Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(30)H(31)NO(6)S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thioethyl group has the exo-anomeric conformation. The hydroxy group forms an intermolecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close π–π contacts with centroid–centroid distances less than 4.0 Å, all with dihedral angles between the interacting π systems of only ≃ 8°, supporting energetically favourable stacking interactions. International Union of Crystallography 2010-11-20 /pmc/articles/PMC3011472/ /pubmed/21589536 http://dx.doi.org/10.1107/S1600536810047069 Text en © Hamark et al. 2010 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 Hamark, Christoffer Landström, Jens Eriksson, Lars Widmalm, Göran Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title | Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title_full | Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title_fullStr | Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title_full_unstemmed | Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title_short | Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-d-glucopyranoside |
title_sort | ethyl 3,6-di-o-benzyl-2-deoxy-n-phthalimido-1-thio-β-d-glucopyranoside |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011472/ https://www.ncbi.nlm.nih.gov/pubmed/21589536 http://dx.doi.org/10.1107/S1600536810047069 |
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