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Thiourea-Cu(OTf)/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors. | LitMetric

AI Article Synopsis

  • A novel glycosylation promoter system is introduced, using thiourea and Cu(OTf) with a bit of iodosuccinimide at room temperature.
  • This method effectively works with 2-azidoselenoglycoside and thioglycoside donors, allowing for smooth conversion to -(2-azido)glycosides.
  • The technique is praised for its ease of use and compatibility with various functional groups, making it a valuable addition to glycosylation methods.

Article Abstract

A novel promoter system for glycosylation is described. A catalytic amount of thiourea and Cu(OTf) together with a slight excess of -iodosuccinimide synergistically promotes glycosylation at room temperature. The combination of reagents applies to some 2-azidoselenoglycoside and thioglycoside donors. A wide range of alcoholic acceptors underwent smooth conversion to -(2-azido)glycosides with good stereoselectivities. In addition, the value of this method has been highlighted by its convenient operation and outstanding functional group compatibility.

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Source
http://dx.doi.org/10.1039/d4ob00064aDOI Listing

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