4.8 Article

Thioperoxide-Mediated Activation of Thioglycoside Donors

Journal

ORGANIC LETTERS
Volume 16, Issue 11, Pages 3102-3105

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol501211z

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Funding

  1. Natural Science Foundation of Zhejiang Province [R4110195]
  2. Science & Technology Department of Zhejiang Province [2013C24004]

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Thioperoxide (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively in the presence of different glycosyl acceptors, giving glycosidation products in high to excellent yields. A plausible activation pathway was also proposed and supported by isolating side-products trifluoromethylphenyl disulfide (CF3SSPh) and alkene (42).

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