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Título: | β-Fragmentation of primary alkoxyl radicals versus hydrogen abstraction: synthesis of polyols and α,ω-differently substituted cyclic ethers from carbohydrates |
Autor: | Boto, Alicia CSIC ORCID ; Hernández, Dácil CSIC ORCID ; Hernández, Rosendo CSIC; Suárez, Ernesto CSIC ORCID | Fecha de publicación: | 28-may-2003 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 68(13): 5310-5319 (2003) | Resumen: | The β-fragmentation of primary alkoxyl radicals, described in many cases as low-yielding and plagued by side reactions, can proceed in satisfactory yields using carbohydrate substrates. The only reaction that can compete significantly with the β-scission is the intramolecular hydrogen abstraction. The ratio of β-fragmentation to hydrogen abstraction can be varied according to the reaction conditions, the stereochemistry of the substituents (e.g., α- or β-anomeric substituents), and the protecting groups chosen. The carbohydrate substrates are easily prepared, and the mild reaction conditions are compatible with most functional groups. The β-scission reaction provides an expedient way toward shorter and less common sugar series and also toward α,ω-differently substituted cyclic ethers. These units are useful building blocks and are present in many natural products with interesting biological activity. | Descripción: | 10 pages, 2 figures, 2 tables, 7 schemes.-- PMID: 12816493 [PubMed].-- Printed version published Jun 27, 2003. | Versión del editor: | http://dx.doi.org/10.1021/jo034442f | URI: | http://hdl.handle.net/10261/16897 | DOI: | 10.1021/jo034442f | ISSN: | 0022-3263 |
Aparece en las colecciones: | (IPNA) Artículos |
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