Journal
TETRAHEDRON
Volume 60, Issue 5, Pages 1057-1064Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.11.084
Keywords
carbohydrates; glycosylation; chemoselective; triflate
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A novel chemoselective glycosylation sequence is described that employs the recently developed BSP/Tf2O and DPS/Tf2O reagent systems to activate thioglycosides. In the first glycosylation event a relatively armed thioglycoside is activated with the BSP/Tf2O activator system and condensed with an acceptor thioglycoside to yield the thiodisaccharide, which is activated with the more potent DPS/Tf2O activator in the next glycosylation event. Quenching of (N-piperidino)phenyl(S-thiophenyl)sulfide triflate, which is formed upon activation of the first thioglycoside, with triethyl phosphite is crucial for a productive glycosylation. (C) 2003 Elsevier Ltd. All rights reserved.
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