Reductive amination of dihydroxyacetone by ammonium salts with sodium cyanoborohydride gives bis(1,3-dihydroxy-isopropyl)amine [BDI] in good yield and high purity. BDI and its diacetonide are hindered nucleophiles but may be further reductively alkylated to form N-alkyl derivatives. BDI is an open chain equivalent of DMDP [2,5-dideoxy-2,5-imino-D-mannitol] but neither BDI nor its N-alkyl derivatives show inhibition of any glycosidase or transferase assayed. BDI may provide an example of an AB4 dendritic monomer.
