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Closed Access item Fragmentation of carbohydrate anomeric alkoxy radicals. synthesis of polyhydroxy piperidines and pyrrolidines related to carbohydrates

Authors:Francisco, Cosme G.
Freire, Raimundo
González Martín, Concepción C.
León, Elisa I.
Riesco-Fagundo, Concepción
Suárez, Ernesto
Issue Date:31-Jan-2001
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 66(5): 1861-1866 (2001)
Abstract: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.
Description:6 pages, 1 table, 4 schemes.-- PMID: 11262138 [PubMed].-- Printed version published Mar 9, 2001.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0057452
Publisher version (URL):http://dx.doi.org/10.1021/jo0057452
Appears in Collections:(IPNA) Artículos

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