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Título : Fragmentation of carbohydrate anomeric alkoxy radicals. synthesis of polyhydroxy piperidines and pyrrolidines related to carbohydrates
Autor : Francisco, Cosme G., Freire, Raimundo, González Martín, Concepción C., León, Elisa I., Riesco-Fagundo, Concepción, Suárez, Ernesto
Fecha de publicación : 31-Jan-2001
Editor: American Chemical Society
Citación : Journal of Organic Chemistry 66(5): 1861-1866 (2001)
Resumen: Imino sugars of the piperidine and pyrrolidine types can be specifically obtained when protected 5-amino-5-deoxyfuranopentoses, 5-amino-5-deoxyfuranohexoses, 6-amino-6-deoxyfuranohexoses, and 6-amino-6-deoxypyranohexoses undergo a tandem alkoxy radical β-fragmentation−intramolecular cyclization reaction. The reaction is promoted by the system: iodosylbenzene−iodine under mild conditions. The tert-butoxycarbonyl, benzyloxycarbonyl, and diphenylphosphinoyl radicals have been studied as amino-protecting groups. Using this methodology, polyhydroxylated pyrrolidines of the d-erythrofuranoses 34 and 35, d-threofuranose 36, l-xylofuranose 42, and d-arabinofuranose 43 series and polyhydroxylated piperidines of the d-arabinopyranose type 37 and 38 were obtained.
Descripción : 6 pages, 1 table, 4 schemes.-- PMID: 11262138 [PubMed].-- Printed version published Mar 9, 2001.
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ISSN: 0022-3263
DOI: 10.1021/jo0057452
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