Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer.

Anthony W McDonagh, Mary F Mahon, Paul V Murphy

Organic letters 2016 Feb 5

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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 α-GalCer (KRN7000).

Citation

Anthony W McDonagh, Mary F Mahon, Paul V Murphy. Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer. Organic letters. 2016 Feb 5;18(3):552-5