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Synlett 2000; 2000(12): 1837-1839
DOI: 10.1055/s-2000-8686
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Synthesis of a Polyhydroxylated Tetrahydro-4H-1,2,3-triazolo[1,5-a]azepin, a Higher Homolog of "Nojiritriazole", and of a Related C-Disaccharide

Kenichi Tezuka* , Philippe Compain, Olivier R. Martin
  • *Department of Chemistry, State University of New York, Binghamton, NY 13902-6016, USA; Fax +33 2 38 41 72 81; E-mail: Olivier.Martin@univ-orleans.fr
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Publication Date:
31 December 2000 (online)

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The first synthesis of a polyhydroxylated tetrahydro-4H-1,2,3-triazolo[1,5-a]azepin derivative (`homonojiritriazole' 7) and of the related C-disaccharide 11 has been achieved from the 5-azido-5-deoxy-d-glucofuranose derivative 4, by way of an acetylide chain-extension and an internal [1,3]-dipolar cycloaddition. Compound 7 was found to be a very weak inhibitor of E. coli α-galactosidase and of isomaltase (α-glucosidase) from baker's yeast.

cycloadditions - iminosugars - C-glycosides - glycosidase inhibitors