ChemInform Abstract: Synthesis of 1,5-Dideoxy-1,5-imino-D-xylonolactam via Acid-Catalyzed Intramolecular Schmidt Rearrangement

Summary 5-Azido-2,3,4-tri-O-benzoyl-5-deoxy-D-xylose diethyl dithioacetal (3) undergoes smooth Lewis acid-catalyzed demercaptalation (boron trifluoride etherate/HgO) to afford the unstable aldehydo-azide 4, which in the presence of Lewis acids yields the tribenzoate 6 of the title compound (7) via an apparent intramolecular Schmidt rearrangement.