Abstract
Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.
Original language | English (US) |
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Pages (from-to) | 61-69 |
Number of pages | 9 |
Journal | Carbohydrate Research |
Volume | 320 |
Issue number | 1-2 |
DOIs | |
State | Published - Jul 20 1999 |
Externally published | Yes |
Keywords
- Glycosyl bromide
- Glycosyl iodide
- Halide-catalyzed anomerization
- In situ anomerization
- Trehalose analogs
- α-Glycosylation
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry