A novel approach to the 1-deoxynojirimycin system: Synthesis from sucrose of 2-acetamido-1,2-dideoxynojirimycin, as well as some 2-N-modified derivatives

6-Azido-1,3,4-tri-O-benzyl-6-deoxy-d-fructofuranose can be easily obtained in two steps from the known 6,6′-diazido-6,6′-dideoxysucrose (available in two steps from sucrose) and cyclized by controlled hydrogenation and concomitant intramolecular reductive amination to give 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-d-mannitol, a partially protected derivative of 1-deoxymannojirimycin. After N-protection, position 2 is regio-specifically available to modification. This novel approach was taken advantage of in a synthesis of 2-acetamido-1,2-dideoxynojirimycin and new analogues thereof. Results of inhibition studies conducted with these new compounds employing N-acetylhexosaminidases of various sources are discussed.