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Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer

McDonagh, Anthony W.
; 
Mahon, Mary F.
; 
Murphy, Paul V.
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http://hdl.handle.net/10379/5940
 https://doi.org/10.13025/15043
Publication Date
2016-01-22
Keywords
Chemistry, Killer t-cells, X-ray crystallography, Glucuronic acid, Stereoselective synthesis, Thioglycoside analog, Efficient synthesis, Protecting group, Glycosyl donors, Facile method, C-arylation
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McDonagh, Anthony W., Mahon, Mary F., & Murphy, Paul V. (2016). Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer. Organic Letters, 18(3), 552-555. doi: 10.1021/acs.orglett.5b03591
Abstract
The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid groups were attached to the anomeric Se atom. An increased amount of TiCl4 and/or higher temperature were needed to ensure completion of the reaction in some cases. Yields were higher for reactions carried out at higher dilution. The reaction was applied to the synthesis of Se-based mimics of the potent immunostimulant alpha-GalCer (KRN7000).
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Publisher
American Chemical Society
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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School of Biological and Chemical Sciences (Scholarly Articles)