General methods for the synthesis of glycopyranosyluronic acid azides

Laiqiang Ying, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

Per-O-acetylated D-glycopyranoses derived from both mono- and disaccharides were first converted to glycosyl iodides and subsequently reacted with an azide source to achieve the stereoselective synthesis of β-D-glycosyl azides after deacetylation. Low-temperature (4°C) TEMPO oxidation of the monosaccharides provided the corresponding uronic acids, which were purified as the free acids. Oxidation of the lactosyl- and cellobiosyl azides resulted in diacid formation. However, 4′,6′-O-benzylidene protection enabled selective oxidation of the C-6 hydroxyl. 2-Acetamido-2-deoxy-D-glycopyranosyl azides were also prepared and converted to uronic acids completing the library synthesis.

Original languageEnglish (US)
Pages (from-to)835-841
Number of pages7
JournalCarbohydrate Research
Volume338
Issue number9
DOIs
StatePublished - Apr 22 2003

Keywords

  • Glycosyl azides
  • TEMPO oxidation
  • Uronic acid azides, unprotected

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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