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 Citations (Scopus)

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

Fingerprint

Iodides
Glycosylation
Octanols
Glycoconjugates
Lactose
Microwaves
Reaction products
Hydroxyl Radical
Nuclear magnetic resonance spectroscopy
Polysaccharides
Magnetic Resonance Spectroscopy
Metals
Cholesterol
Acids
lactosides
trimethylsilyl iodide

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide. / Davis, Ryan A.; Fettinger, James C.; Gervay-Hague, Jacquelyn.

In: Tetrahedron Letters, Vol. 56, No. 23, 46284, 01.12.2014, p. 3690-3694.

Research output: Contribution to journalArticle

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