Studies for the Multimerization of DAB-1-Based Imino Sugars through Iteration of the Nitrone Cycloaddition/Ring-Opening/ Allylation Sequence

Multivalent imino sugars have gained the attention of the research community in the last ten years. We report herein the proof of principle for an original synthetic strategy to build multivalent imino sugars based on the natural DAB-1 11 moiety as the bioactive epitope. The synthesis relies on the iteration of three selective and high-yielding steps (1,3-dipolar cycloaddition to nitrone 1, N-O bond cleavage of the adduct and selective N- and/or O-allylation), and allows the preparation of different topologies of the final DAB-1 clusters.