SYNTHESIS, REACTIVITY AND SELECTIVITY STUDIES ON CARBAGLYCAL-DERTVED W-PROTECTED AZIRIDINES 3α AND 3β AS NEW USEFUL CARBASUGARS SYNTHETIC TOOLS

摘要

Carbasugars, analogs of real sugars in which the endocyclic oxygen is replaced by a methylene group, are part of interesting biomolecules, such as pseudoglycoproteins, pseudoglycolipids and other conjugates. In nature there are a several fully oxygenated carbasugars or aminocarbasugar derivatives, such as Valienamine and its conjugated Validamycin A, displaying an antibacterial activity (Scheme 1). Our interest in carbasugars, started with the synthesis of vinyl epoxides (-)-1α and (-)-1β, the carba-analogs of the previously studied D-galactal- and D-allal- derived epoxides 2α and 2β, respectively, has been now directed towards the corresponding iV-protected aziridines 3α and 3β, both racemic and as pure enantiomers. Actually, the use of these aza-heterocycles would have made the introduction of a free, or N-protected, amino group on C4 of a carbasugar system possible.