An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-d-mannitol and arylamino derivatives

1-Amino-2,5-anhydro-1-deoxy-d-mannitol and a series of arylamino derivatives were prepared by nitrous acid deamination of 2-amino-2-deoxy-d-glucose and subsequent reductive amination of the resulting 2,5-anhydro-d-mannose. Some of these compounds showed an enhanced affinity for the hexose transporter of Trypanosoma brucei as compared to d-fructose.