Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• subsequent reductive amination. This strategy involving the nucleophilic opening of a cis-cyclic sulfate by sodium azide is to our knowledge the first example in C8-series. It revealead to be an efficient alternative to the nucleoplilic opening of an epoxide moiety which proved unsuccessful in this

• purification by ion-exchange chromatography, the targeted aminocyclitol 15 [20] (95% overall yield from 11). Alternatively, to obtain an analog of voglibose, the amine function of 13 could be alkylated via a reductive amination [39] with a dihydroxyacetone derivative. Thus, treatment of the amine 13 by the

• . According to this strategy and to the nature of the ketones involved in the final reductive amination, various aminocyclitols could be synthesized. Thus, in this study two carbasugars and four aminocyclitols were obtained. Biological evaluation of these compounds towards 24 commercially available