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(±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine
The crystal structure of the title compound, C(30)H(38)N(2)O(5)Si, has been investigated to establish the relative stereochemistry at the spiro ring junction and the two anomeric centres. Each of the O atoms in the tetrahydropyran rings adopts an axial position on the neighbouring ring. This bis-...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961017/ https://www.ncbi.nlm.nih.gov/pubmed/21202106 http://dx.doi.org/10.1107/S1600536808006727 |
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author | Choi, Ka Wai Brimble, Margaret A. Groutso, Tania |
author_facet | Choi, Ka Wai Brimble, Margaret A. Groutso, Tania |
author_sort | Choi, Ka Wai |
collection | PubMed |
description | The crystal structure of the title compound, C(30)H(38)N(2)O(5)Si, has been investigated to establish the relative stereochemistry at the spiro ring junction and the two anomeric centres. Each of the O atoms in the tetrahydropyran rings adopts an axial position on the neighbouring ring. This bis-diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect. The silyl-protected hydroxymethyl and uracil substituents adopt equatorial positions on their associated tetrahydropyran rings, thereby minimizing unfavourable steric interactions. The dimeric (2′R*,6′R*,8′R*)- and (2′S*,6′S*,8′S*)-uridine units are connected to each other across crystallographic inversion centres via intermolecular N—H⋯O hydrogen bonds. |
format | Text |
id | pubmed-2961017 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29610172010-12-30 (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine Choi, Ka Wai Brimble, Margaret A. Groutso, Tania Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound, C(30)H(38)N(2)O(5)Si, has been investigated to establish the relative stereochemistry at the spiro ring junction and the two anomeric centres. Each of the O atoms in the tetrahydropyran rings adopts an axial position on the neighbouring ring. This bis-diaxial conformation is adopted, thus gaining maximum stablization from the anomeric effect. The silyl-protected hydroxymethyl and uracil substituents adopt equatorial positions on their associated tetrahydropyran rings, thereby minimizing unfavourable steric interactions. The dimeric (2′R*,6′R*,8′R*)- and (2′S*,6′S*,8′S*)-uridine units are connected to each other across crystallographic inversion centres via intermolecular N—H⋯O hydrogen bonds. International Union of Crystallography 2008-03-14 /pmc/articles/PMC2961017/ /pubmed/21202106 http://dx.doi.org/10.1107/S1600536808006727 Text en © Choi et al. 2008 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 Choi, Ka Wai Brimble, Margaret A. Groutso, Tania (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title | (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title_full | (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title_fullStr | (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title_full_unstemmed | (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title_short | (±)-1-{8′-(tert-Butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
title_sort | (±)-1-{8′-(tert-butyldiphenylsilyloxymethyl)-1′,7′-dioxaspiro[5.5]undecan-2′-yl}uridine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961017/ https://www.ncbi.nlm.nih.gov/pubmed/21202106 http://dx.doi.org/10.1107/S1600536808006727 |
work_keys_str_mv | AT choikawai 18tertbutyldiphenylsilyloxymethyl17dioxaspiro55undecan2yluridine AT brimblemargareta 18tertbutyldiphenylsilyloxymethyl17dioxaspiro55undecan2yluridine AT groutsotania 18tertbutyldiphenylsilyloxymethyl17dioxaspiro55undecan2yluridine |