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Synthesis of monosaccharide-fused azetidines

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
299
Issue
4
Identifiers
DOI: 10.1016/s0008-6215(97)00015-3
Keywords
  • Tosylate
  • Nucleophilic Substitution
  • Monosaccharide
  • Azetidine

Abstract

Abstract 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.

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