1-C-(2′-Oxoalkyl) glycosides as latent α,β-unsaturated conjugates. Synthesis of aza-C-glycosides by an intramolecular hetero-Michael addition

Tian Yi, An Tai Wu, Shih Hsiung Wu, Wei Zou

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

1-C-(2′-Oxoalkyl)-5-azido-5-deoxy-glycofuranosides were used as latent substrates for intramolecular hetero-Michael addition. Reduction of the azido groups by catalytic hydrogenation followed by base treatment produced 2′-ester and 2′-ketone aza-C-glycopyranosides. The conjugation addition was stereoselective in favor of aza-C-glycosides with equatorial substitutions at the pseudo anomeric center.

Original languageEnglish
Pages (from-to)11716-11722
Number of pages7
JournalTetrahedron
Volume61
Issue number49
DOIs
Publication statusPublished - 2005 Dec 5

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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