172539-17-2

Upstream product

• 172539-16-1 5-azido-2,3,4-tri-O-benzoyl-5-deoxy-D-xylose diethyl dithioacetal 
• 4711-03-9 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 98-88-4 benzoyl chloride 
• 172721-18-5 (2R,3S,4R)-5-Azido-1,1-bis-ethylsulfanyl-pentane-2,3,4-triol 

Downstream Products

• 172539-19-4 2,3,4-tri-O-benzoyl-D-xylono-1,5-lactam 

Relevant academic research and scientific papers

Synthesis of 1,5-dideoxy-1,5-imino-D-xylonolactam via acid-catalyzed intramolecular Schmidt rearrangement

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.