%0 Journal Article
%A Yasomanee, Jagodige
P.
%A Demchenko, Alexei V.
%D 2012
%T Effect of Remote Picolinyl
and Picoloyl Substituents
on the Stereoselectivity of Chemical Glycosylation
%U https://acs.figshare.com/articles/journal_contribution/Effect_of_Remote_Picolinyl_and_Picoloyl_Substituents_on_the_Stereoselectivity_of_Chemical_Glycosylation/2460592
%R 10.1021/ja307355n.s001
%2 https://acs.figshare.com/ndownloader/files/4103284
%K glycosidic linkages
%K glycosylation reactions
%K glycosyl acceptor
%K glycosyl acceptor counterparts
%K glycosyl donor
%K Remote Picolinyl
%K Picoloyl Substituents
%X O-Picolinyl and O-picoloyl
groups
at remote positions (C-3, C-4, and C-6) can mediate glycosylation
reactions by providing high or even complete facial selectivity for
the attack of the glycosyl acceptor. The set of data presented herein
offers a strong evidence of the intermolecular H-bond tethering between
the glycosyl donor and glycosyl acceptor counterparts while providing
a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging
glycosidic linkages including α-gluco, β-manno, and β-rhamno
have seen obtained with high or complete stereocontrol.
%I ACS Publications