Synthesis of a novel α-glucoside of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-d-mannitol via enzymatic glucosylation of 5-azido-5-deoxy-d-fructopyranose
✍ Scribed by Karl Dax; Michael Ebner; Roland Peinsipp; Arnold E. Stütz
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 127 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Regio-and stereoselective enzymatic glucosylation of 5-azido-5-deoxy-D-fructopyranose with the aid of commerically available 0t-glucosidase from yeast allows easy access to the corresponding 4-O-~t-D-glucopyranosyl derivative of this non-natural ketose. This disaccharide gives, in one step, access to 2,5-dideoxy-3-O-~-Dglucopyranosyl-2,5-imino-D-mannitol.
📜 SIMILAR VOLUMES
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 exce
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