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

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• 作者：Anthony W. McDonagh ; Mary F. Mahon ; Paul V. Murphy
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：552-555
• 全文大小：459K
• ISSN：1523-7052

文摘

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).