An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: The D-gluco case

P. Pádár, P. Forgó, Z. Kele, N. M. Howarth, L. Kovács

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Abstract

The diastereoselective intramolecular 1,3-dipolar cycloaddition reaction of unsaturated nitrones, derived from methyl α-D-glucopyranoside with 2-furaldehyde and 2-(benzyloxy)acetaldehyde has been studied. In our pevious studies with 2-furaldehyde, the cycloaddition resulted 3 diastereoisomers in a 3:1:1 ratio. In this article, how the number of the possible isomers generated by 1,3-cycloaddition could be reduced from 4 to 1 when 2-(benzyloxy)acetaldehyde was employed as an aldehyde is shown.

Original languageEnglish
Pages (from-to)743-745
Number of pages3
JournalNucleosides, Nucleotides and Nucleic Acids
Volume24
Issue number5-7
DOIs
Publication statusPublished - Oct 20 2005

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ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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