Synthesis of monosaccharide-fused azetidines

Article abstract of DOI:10.1016/S0008-6215(97)00015-3

Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by ¹H and ¹³C NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments.