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Practical synthesis of N-alkyl-N-glycosylhydroxylamines, multitalented precursors of enantiomerically pure nitrones

✍ Scribed by Stefano Cicchi; Massimo Corsi; Marco Marradi; Andrea Goti

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 108 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00372-6

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✦ Synopsis

A practical synthesis of N-benzyl-N-glycosylhydroxylamines 3 (R=CH 2 Ph) is reported. The ability of these compounds to act as versatile synthetic intermediates is demonstrated by their oxidation followed by cycloaddition to N-glycosyl isoxazolidines and by the novel direct cycloaddition as masked acyclic, highly functionalized chiral nitrones.

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