Synthesis of Alanosine

Abstract

Abstract Dl-2-Ammo-3-(N-tosyl-N-benzyloxyamino)propionic acid (Dl-V) was synthesized starting from ethyl 2,3-dibromopropionate and N-tosyl-O-benzylhydroxylamine. l-2-Benzoylamino-3-(N-benzoyl-N-hydroxyamino)propionic acid anilide (l XIV) obtained via the enzymatic resolution of Dl-2-benzoylamino-3-benzyloxyaminopropionic acid (Dl-IX) was converted by acid hydrolysis to l-2-amino-3-hydroxyaminopropionic acid (l-II). The nitrosation product of the amino-hydroxyamino acid (l-II) was identical with alanosine (l-I).