Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes

The utility of the Beckmann rearrangement for the synthesis of glycoside-derived lactams, from oxime precursors, is described. The rearrangement is demonstrated to occur in moderate to very good synthetic yield, and with excellent regioselectivity, using 2,4,6-trichloro[1,3,5]triazine (TCT) as an effective and mild promoter.