SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-XYLONOLACTAM VIA ACID-CATALYZED INTRAMOLECULAR SCHMIDT REARRANGEMENT

Authors
NORRIS P HORTON D LEVINE BR
Citation
P. Norris et al., SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-XYLONOLACTAM VIA ACID-CATALYZED INTRAMOLECULAR SCHMIDT REARRANGEMENT, Tetrahedron letters, 36(43), 1995, pp. 7811-7814
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
43
Year of publication
1995
Pages
7811 - 7814
Database
ISI
SICI code
0040-4039(1995)36:43<7811:SO1VAI>2.0.ZU;2-S
Abstract
5-Azido-2,3,4-tri-Obenzoyl-5-deoxy-D-xylose diethyl dithioacetal (3) u ndergoes smooth Lewis acid-catalyzed demercaptalation (boron trifluori de etherate/HgO) to afford the unstable aldehydo-azide 4, which in the presence of Lewis acids yields the tribenzoate 6 of the title compoun d (7) via an apparent intramolecular Schmidt rearrangement.