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Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation

Farrell, Mark P.
; 
Doyle, Lisa M.
; 
Murphy, Paul V.
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Identifiers
http://hdl.handle.net/10379/15195
 https://doi.org/10.13025/14933
Publication Date
2018-05-26
Keywords
Carbohydrates, Anomerisation, Glycoside, Lewis acid, Protecting groups, Reactivity
Type
journal article
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Citation
Farrell, Mark P., Doyle, Lisa M., & Murphy, Paul V. (2018). Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation. Tetrahedron Letters, 59(28), 2726-2731. doi: https://doi.org/10.1016/j.tetlet.2018.05.076
Abstract
Lewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-d-glucopyranosides was determined to determine how particular acyl protecting groups and their location influence reactivity towards a Lewis acid promoted reaction. The replacement of acetyl groups with benzoyl groups led to reduced reactivity when located at O-3, O-4 and O-6. However a reactivity increase was observed when the acetyl group was replaced by a benzoyl group at O-2. The 2,3,4,6-tetra-O-(4-methoxy)benzoate had an⠯⠼2-fold increase in rate when compared to the tetrabenzoate.
Funder
Science Foundation Ireland
European Regional Development Fund
Irish Research Council
Roche Ireland Ltd
Publisher
Elsevier
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Rights
CC BY-NC-ND
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