TY - JOUR
T1 - Lewis acid induced anomerization of Se-glycosides. Application to synthesis of α-Se-GalCer
AU - McDonagh, Anthony W.
AU - Mahon, Mary F.
AU - Murphy, Paul V.
PY - 2016/2/5
Y1 - 2016/2/5
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=84957590949&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1021/acs.orglett.5b03591
U2 - 10.1021/acs.orglett.5b03591
DO - 10.1021/acs.orglett.5b03591
M3 - Article
AN - SCOPUS:84957590949
SN - 1523-7060
VL - 18
SP - 552
EP - 555
JO - Organic Letters
JF - Organic Letters
IS - 3
ER -