Chemoselective glycosylations using sulfonium triflate activator systems

A novel chemoselective glycosylation sequence is described that employs the recently developed BSP/Tf 2O and DPS/Tf 2O reagent systems to activate thioglycosides. In the first glycosylation event a relatively armed thioglycoside is activated with the BSP/Tf 2O activator system and condensed with an...

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Bibliographic Details
Published in:Tetrahedron 2004-01, Vol.60 (5), p.1057-1064
Main Authors: Codée, Jeroen D.C, van den Bos, Leendert J, Litjens, Remy E.J.N, Overkleeft, Herman S, van Boeckel, Constant A.A, van Boom, Jacques H, van der Marel, Gijs A
Format: Article
Language:English
Subjects:
Carbohydrates
Chemoselective
Glycosylation
Triflate
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Summary:A novel chemoselective glycosylation sequence is described that employs the recently developed BSP/Tf 2O and DPS/Tf 2O reagent systems to activate thioglycosides. In the first glycosylation event a relatively armed thioglycoside is activated with the BSP/Tf 2O activator system and condensed with an acceptor thioglycoside to yield the thiodisaccharide, which is activated with the more potent DPS/Tf 2O 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.11.084