Journal
TETRAHEDRON
Volume 64, Issue 1, Pages 92-102Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.10.087
Keywords
1,2-cis-glycosylation; alpha-Glucoside; stereoselective; solvent effect
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Construction of three continuous 1,2-cis-alpha-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d(7)) groups. It enabled facile evaluation of yield and stereoselectivity with H-1 NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the a-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glc alpha 1-2Glc alpha 1-3Glc alpha l-3Man (GlC(3)Man(1)), which was achieved in 86% overall stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.
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