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  • Title: Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters.
    Author: Vidadala SR, Thadke SA, Hotha S.
    Journal: J Org Chem; 2009 Dec 04; 74(23):9233-6. PubMed ID: 19886637.
    Abstract:
    An orthogonal activation strategy with propargyl and n-pentenyl glycosides has been identified. According to this methodology, n-pentenyl glycosides can be selectively activated with NIS/TMSOTf in the presence of either armed or disarmed propargyl O-glycosides. In addition, we report herein that propargyl 1,2-orthoesters can be selectively activated with AuBr(3) in CH(2)Cl(2) at room temperature in the presence of n-pentenyl glycosides. Similarly, pentenyl 1,2-orthoesters can be selectively activated with NIS/Yb(OTf)(3) in the presence of propargyl glycosides.
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