Synthesis of azasugars. Part 1. Isomerization of polyhydroxylated piperidines

Article abstract of DOI:10.1016/0040-4039(96)00096-2

N-Benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol and L-gulitol undergo easy isomerization, mainly either by ring contraction, or either by SN₂ inversion at C2. This isomerization performed by bis-hydroxyl activation allows to access to 2,5-dideoxy-2,5-imino-L-iditol, 5-epi-DNJ, DMDP, and DMJ.