A Short and Convenient Synthesis of 1-Deoxymannojirimycin and <i>N</i>-Oxy Analogues from <scp>d</scp>-Fructose

Abstract

Ketonitrone 8 was prepared from D-fructose as an inexpensive starting material and was used in a stereoselective synthesis of 1-deoxymannojirimycin (DMJ, 4), of its previously unknown N-hydroxy analogue 15, and of the polyhydroxylated ketonitrone 14. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. Disappointingly, the polyhydroxylated nitrone 14 inhibited none of these enzymes. However, N-hydroxy-DMJ (15) exhibited a moderate and non-selective activity toward the snail beta-mannosidase EC 3.2.1.25.