%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