| DOI | Trouver le DOI : https://doi.org/10.1021/jo3024973 |
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| Auteur | Rechercher : Zou, W.1; Rechercher : Vembaiyan, K.1 |
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| Affiliation | - Conseil national de recherches du Canada. Institut des sciences biologiques du CNRC
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| Format | Texte, Article |
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| Sujet | Anomeric configuration; C-glycosides; Chemical yields; Enamine intermediates; Epimerization; Intramolecular cyclizations; Nucleophilic substitutions; Pyrrolidines; Cyclization; Heptane; Stereoselectivity; Sugars; 7 oxabicyclo [2 2 1] heptane; 8 oxabicyclo [3 2 1]octane; glycoside; heptane; octane; pyrrolidine derivative; unclassified drug; bicyclo compound; C glycoside; C-glycoside; cycloheptane derivative; cyclooctane derivative; monosaccharide; chemical reaction; chemical structure; cyclization; epimerization; nucleophilicity; stereochemistry; synthesis; chemistry; cyclization; stereoisomerism; Bicyclo Compounds; Cyclization; Cycloheptanes; Cyclooctanes; Molecular Structure; Monosaccharides; Stereoisomerism |
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| Résumé | A simple and effective method for the synthesis of 7-oxabicyclo[2.2.1] heptanes and 8-oxabicyclo[3.2.1]octanes from acetonyl C-glycoside substrates is described, which involves an intramolecular cyclization reaction through a nucleophilic substitution at C-5 or C-6 of C-glycosides by a 2′-enamine intermediate formed in the presence of pyrrolidine. Because anomeric epimerization occurs under these conditions, C-glycoside substrates with either anomeric configuration were converted to the same product(s) in same stereoselectivity and similar chemical yield. © 2013 American Chemical Society. |
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| Date de publication | 2013 |
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| Dans | |
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| Langue | anglais |
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| Publications évaluées par des pairs | Oui |
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| Numéro NPARC | 21269925 |
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| Exporter la notice | Exporter en format RIS |
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| Signaler une correction | Signaler une correction (s'ouvre dans un nouvel onglet) |
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| Identificateur de l’enregistrement | 8859ff11-0861-49b5-82f3-ed151ee60d6d |
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| Enregistrement créé | 2013-12-13 |
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| Enregistrement modifié | 2020-04-22 |
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