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

AuthorsFrancisco, Cosme G. ; Freire, Raimundo ; González Martín, Concepción C. ; León, Elisa I. ; Riesco-Fagundo, Concepción ; Suárez, Ernesto
Issue Date31-Jan-2001
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 66(5): 1861-1866 (2001)
AbstractImino 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.
Description6 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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