REDUCTIVE AMINATION OF ALDOHEXOSES WITH MONOFUNCTIONAL AND BIFUNCTIONAL ALKYL AMINES - CONVERSION OF CARBOHYDRATES INTO EDTA TYPE COMPLEXING AGENTS

It is shown by H-1 and C-13 NMR spectroscopy (1D and 2D) that beta-N-propylgalactosylamine (5a) is the major species present in an equimolar aqueous solution of D-galactose (1a) and propylamine (PA). In equimolar solutions of aldohexoses (1a-c) and ethylenediamine (EN) or 1,3-diaminopropane (DAP) in addition to mono- (9) and diglycosylamines (12) tetra-imidazole (8, n=1) and hexahydropyrimidine derivatives (8, n=2), respectively, are formed. Hydrogenation of equimolar solutions of aldohexoses (1a-c) and primary amines (PA, EN, and DAP) at 100 atm. and 50 degrees C, using 5% Pt on carbon as the catalyst, gave amino sugars 13-16 in good yields. Carboxymethylation of 14a-b resulted in sugar based EDTA type complexing agents (17a-b) with promising chelating abilities towards Cd(II) and Ca(II) at high pH.