Synthesis of new stereoisomeric Nitrate esters derived form isosorbide-mononitrate II:bicyclic #delta#-lactams and tetrahydrofuran derivatives

摘要

The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1.4:3.6-dianhydro-D-glucitol-5-(or -2-)nitrate -2-(or-5-)ketoximes (4b and 8),respectively.The bicyclic #delta#-lactams,(1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicylo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-niprepared by the Beckmann rearragement of nitrones 14b and 17b,respectively.The stereoisomeric #delta#-lactams.N-methyl-7-endo-benzoyloxy-(15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from te correspoding nitrones 14a and 17a,respectively.