Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide

Ryan A. Davis, James C. Fettinger, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Abstract The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The β-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of α-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides α-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.

Original languageEnglish (US)
Article number46284
Pages (from-to)3690-3694
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - Dec 1 2014

Keywords

  • 1,2-cis
  • Glycosyl iodide glycosylation
  • H. pylori
  • Mechanism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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