Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates

Abstract

A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.