Peer-Reviewed Journal Details
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McDonagh, AW,Mahon, MF,Murphy, PV
2016
February
Organic Letters
Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of alpha-Se-GalCer
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Optional Fields
KILLER T-CELLS X-RAY CRYSTALLOGRAPHY GLUCURONIC-ACID STEREOSELECTIVE-SYNTHESIS THIOGLYCOSIDE ANALOG EFFICIENT SYNTHESIS PROTECTING GROUP GLYCOSYL DONORS FACILE METHOD C-ARYLATION
18
552
555
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).
10.1021/acs.orglett.5b03591
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