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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

✍ Scribed by Tanja M. Wrodnigg; Arnold E. Stütz; Steven G. Withers

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
179 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-l-dibenzylamino-l,5dideoxy-D-fructopyranose, the new l-amino-l,2,5-trideoxy-2,5-ilnino-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.

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