Tetrahedron Letters p. 7811 - 7814 (1995)
Update date:2022-08-03
Topics:
Norris, Peter
Horton, Derek
Levine, Brett R.
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.
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