SYNTHESIS OF THE 1-AMINO-ALDITOLS DERIVED FROM CELLOBIOSE, LACTOSE AND MALTOSE - A COMPREHENSIVE NMR-STUDY OF SOME ALDITOLS AND AMINO-ALDITOLS

Gram quantities of the 1-amino-alditols derived from cellobiose, lactose and maltose were synthesized in 80-90% yield via a reductive amination with benzylamine and subsequent catalytic removal of the benzyl group at atmospheric hydrogen pressure. The 1-amino-alditols together with the products from direct reduction of cellobiose, lactose and six maltooligosaccharides (d.p. 2-7) were fully characterized by NMR. Assignment and analysis was done from a combination of 1D H-1 and C-13 spectra and 2D H-1-H-1 COSY and C-13-H-1 correlation experiments. C-13 chemical shift pH titration curves for the amino-alditols are presented.