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 › peer-review

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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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.",

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T1 - Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide

AU - Davis, Ryan A.

AU - Fettinger, James C.

AU - Gervay-Hague, Jacquelyn

PY - 2014/12/1

Y1 - 2014/12/1

N2 - 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.

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.

KW - 1,2-cis

KW - Glycosyl iodide glycosylation

KW - H. pylori

KW - Mechanism

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

Abstract

Keywords

ASJC Scopus subject areas

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