Abstract
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.
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