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Synthesis of 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol, a novel analogue of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, via an Amadori rearrangement of 5-azido-5-deoxy-D-glucofuranose

TitleSynthesis of 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol, a novel analogue of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, via an Amadori rearrangement of 5-azido-5-deoxy-D-glucofuranose
Publication TypeJournal Article
Year of Publication1997
AuthorsWrodnigg, TM, Stutz, AE, Withers, SG
JournalTETRAHEDRON LETTERS
Volume38
Pagination5463-5466
Date PublishedAUG 4
ISSN0040-4039
Abstract

By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-dibenzylamino-1,5-dideoxy-D-fructopyranose, the new 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and excellent overall yield. Likewise, other amines and/or other 5-modified hexofuranoses can be used to advantage. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to 1-aminodeoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. (C) 1997 Elsevier Science Ltd.

DOI10.1016/S0040-4039(97)01198-2