Iminosugars are polyhydroxylated heterocycles with an endocyclic nitrogen . Iminosugars have been of interest in drug discovery. Nojirimycin, a known glycosidase inhibitor, is unstable due to the labile N,O-acetal function; a-Homonojirimycin is a stable C-glycoside analogue.A route for the stereoselective preparation of iminosugar C-glycosides including a tandem allylic azide rearrangement5 � Huisgen cycloaddition as a key step has been investigated. The results from this investigation will be presented.

Tandem allylic azide rearrangement and cycloaddition in the synthesis of iminosugars

245th National Meeting (2013)

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