Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 23, Pages 9233-9236Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901837z
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- CSIR-New Delhi [NWP0036-B]
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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 AuBr3 in CH2Cl2 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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