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

Anthony W. McDonagh, Mary F. Mahon, Paul V. Murphy

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

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 α-GalCer (KRN7000).

Original languageEnglish
Pages (from-to)552-555
Number of pages4
JournalOrganic Letters
Volume18
Issue number3
Early online date22 Jan 2016
DOIs
Publication statusPublished - 5 Feb 2016

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