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

doi:10.1016/j.tetlet.2015.05.012

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Article number	46284
Pages (from-to)	3690-3694
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.05.012
State	Published - 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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Davis, R. A., Fettinger, J. C., & Gervay-Hague, J. (2014). Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide. Tetrahedron Letters, 56(23), 3690-3694. [46284]. https://doi.org/10.1016/j.tetlet.2015.05.012

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AB - 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.

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KW - H. pylori

KW - Mechanism

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