Orthogonal Activation of Propargyl and n-Pentenyl Glycosides and 1,2-Orthoesters

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• 作者：Srinivasa Rao Vidadala ; Shivaji A. Thadke ; Srinivas Hotha
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：December 4, 2009
• 年：2009
• 卷：74
• 期：23
• 页码：9233-9236
• 全文大小：768K
• 年卷期：v.74,no.23(December 4, 2009)
• ISSN：1520-6904

文摘

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.