A. Kilonda, E. Dequeker, F. Compernolle
Jan 16, 1995
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron
Abstract
Abstract The title compound 6 , [1R-(6 endo , 7 exo )]-8-oxa-3-azabicyclo[3.2.1]octane-6,7-diol, was derived in nine steps from 1-amino-1-deoxy-D-glucitol 2 . The key step was the acid catalyzed rearrangement of epoxide 3 to the 2,5- cis -disposed hydrofuran compound 5 . Linkage of the 2,5-substituents, to form the bridged secondary amine 23 , proceeded via mesylation of 6-OH and deprotection of 1-NH 2 . Further O -debenzylation and (or) N -substitution afforded the aminodiol 6 and various N -alkylated derivatives. On basis of 1 H NMR analysis the chair form was assigned to the bridged morpholine ring.