Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose

Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-l-erythrose and 4-amino-5-deoxy-l-ribose series were synthesised by asymmetric hetero-Diels–Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose were potent β-d-glucosidase, α-d-mannosidase, α- and β-d-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of α-d-mannosidase.