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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...

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Detalles Bibliográficos
Autores principales: Hamark, Christoffer, Landström, Jens, Eriksson, Lars, Widmalm, Göran
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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