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

Author:
McDonagh, Anthony W., Mahon, Mary F., Murphy, Paul V.
Source:
Organic letters 2016 v.18 no.3 pp. 552-555
ISSN:
1523-7052
Subject:
Lewis acids, chemical reactions, chemical structure, galacturonic acid, glycosides, immunostimulants, lipids, organic compounds, selenium, temperature
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).
Agid:
5792312