Cis- and trans-3-Azido-Oxetan-2-Carboxylate Scaffolds: Hexamers of Oxetane cis-b-Amino Acids.

Abstract

Efficient synthesis of both cis- and trans-3-azido-oxetane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-β-amino acids into oligomers; the synthesis of a series of protected β-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-l-altronate are reported.