328533-50-2Relevant academic research and scientific papers
Fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of polyhydroxy piperidines and pyrrolidines related to carbohydrates
Francisco,Freire,Gonzalez,Leon,Riesco-Fagundo,Suarez
, p. 1861 - 1866 (2007/10/03)
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.
