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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-...

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Detalles Bibliográficos
Autores principales: Choi, Ka Wai, Brimble, Margaret A., Groutso, Tania
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
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.
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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
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