SYNTHESIS OF NITROGEN-15-LABELED 2-AMINO(GLYCOFURANO)OXAZOLINES via GLYCSYLAMINE INTERMEDIATES

Article abstract of DOI:10.1016/0008-6215(83)88113-0

A new, efficient synthesis of doubly (15)N-labeled 2-amino-oxazoline derivatives of pentoses and hexoses has been delineated that involves treatment either of unprotected or O-isopropylidenated glycosylamines with cyanamide-(15)N2 in methanol to give 2-amino(glycofurano)oxazolines-(15)N2.A probable mechanism for these reactions is presented.These techniques provide a practical means by which a variety of stable or radioactive isotopes can be introduced into any of several known, clinically significant pyrimidine anhydronucleosides, such as 2,2'-anhydro-(1-β-D-arabinofuranosylcytosine)(cyclo-C).