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 | |
State | Published - Dec 1 2014 |
Keywords
- 1,2-cis
- Glycosyl iodide glycosylation
- H. pylori
- Mechanism
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery