Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid

Paola Rota, Paolo La Rocca, Valentina Franco, Pietro Allevi

Research output: Contribution to journalArticlepeer-review

Abstract

The facile syntheses of previously unreported 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid are herein described. The procedure involves a ring-opening of the 4,5-oxazoline of N-acetylneuraminic acid, the acylation of the intermediate free amine, its conversion into the 4,5-oxazoline of N-glycolylneuraminic acid and the subsequent Ferrier reaction or C4 nucleophilic substitution.

Original languageEnglish
Article number131699
JournalTetrahedron
Volume76
Issue number49
DOIs
Publication statusPublished - Dec 4 2021

Keywords

  • Ferrier reaction
  • Glycals
  • N-Glycolylneuraminic acid
  • Oxazoline of sialic acid
  • Sialidase inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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