873093-23-3Relevant academic research and scientific papers
Effect of remote picolinyl and picoloyl substituents on the stereoselectivity of chemical glycosylation
Yasomanee, Jagodige P.,Demchenko, Alexei V.
supporting information, p. 20097 - 20102 (2013/02/23)
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.
How the arming participating moieties can broaden the scope of chemoselective oligosaccharide synthesis by allowing the inverse armed-disarmed approach
Smoot, James T.,Demchenko, Alexei V.
experimental part, p. 8838 - 8850 (2009/04/05)
(Chemical Equation Presented) A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety,
Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis
Smoot, James T.,Pornsuriyasak, Papapida,Demchenko, Alexei V.
, p. 7123 - 7126 (2007/10/03)
(Chemical Equation Presented) Armed and dangerous: A new armed-disarmed glycosylation strategy (see picture) allows chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages through the use of a 2-O-picolyl moiety. This neighbo
