2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose

The title compound, C(20)H(26)O(7), was prepared by esterification of 2,3;5,6-di-O-isopropyl­idene-α-d-mannofuran­ose with phenyl­acetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) con­ditions. The solid-state structure confirms the retention of t...

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Detalles Bibliográficos
Autores principales: Sacui, Iulia A., Norris, Peter, Zeller, Matthias
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3008108/
https://www.ncbi.nlm.nih.gov/pubmed/21588686
http://dx.doi.org/10.1107/S1600536810032368
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author Sacui, Iulia A.
Norris, Peter
Zeller, Matthias
author_facet Sacui, Iulia A.
Norris, Peter
Zeller, Matthias
author_sort Sacui, Iulia A.
collection PubMed
description The title compound, C(20)H(26)O(7), was prepared by esterification of 2,3;5,6-di-O-isopropyl­idene-α-d-mannofuran­ose with phenyl­acetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) con­ditions. The solid-state structure confirms the retention of the α-configuration at the anomeric C atom. The compound is characterized by a relatively rigid framework with only a few degrees of freedom. Comparison with other di-O-isopropyl­idenemannofuran­ose derivatives shows the main differences to be associated with the flexible dimethyl­dioxolane ring, and that there are only small differences for the 2,3-O-isopropyl­idene-α-d-manno­furan­ose backbone. The packing is marked by a large number of weak C—H⋯O inter­actions.
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spelling pubmed-30081082010-12-30 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose Sacui, Iulia A. Norris, Peter Zeller, Matthias Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(20)H(26)O(7), was prepared by esterification of 2,3;5,6-di-O-isopropyl­idene-α-d-mannofuran­ose with phenyl­acetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) con­ditions. The solid-state structure confirms the retention of the α-configuration at the anomeric C atom. The compound is characterized by a relatively rigid framework with only a few degrees of freedom. Comparison with other di-O-isopropyl­idenemannofuran­ose derivatives shows the main differences to be associated with the flexible dimethyl­dioxolane ring, and that there are only small differences for the 2,3-O-isopropyl­idene-α-d-manno­furan­ose backbone. The packing is marked by a large number of weak C—H⋯O inter­actions. International Union of Crystallography 2010-08-18 /pmc/articles/PMC3008108/ /pubmed/21588686 http://dx.doi.org/10.1107/S1600536810032368 Text en © Sacui 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
Sacui, Iulia A.
Norris, Peter
Zeller, Matthias
2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title_full 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title_fullStr 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title_full_unstemmed 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title_short 2,3;5,6-Di-O-isopropyl­idene-1-O-(2-phenyl­acet­yl)-α-d-mannofuran­ose
title_sort 2,3;5,6-di-o-isopropyl­idene-1-o-(2-phenyl­acet­yl)-α-d-mannofuran­ose
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3008108/
https://www.ncbi.nlm.nih.gov/pubmed/21588686
http://dx.doi.org/10.1107/S1600536810032368
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AT norrispeter 2356dioisopropylidene1o2phenylacetyladmannofuranose
AT zellermatthias 2356dioisopropylidene1o2phenylacetyladmannofuranose

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