Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters.
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.
Vidadala
Srinivasa Rao
SR
Division of Organic Chemistry, Combi Chem-BioResource Center, National Chemical Laboratory (CSIR), Dr. Homi Bhabha Road, Pune 411 008, India.
Thadke
Shivaji A
SA
Hotha
Srinivas
S
D000480:Alkynes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D008722:Methods
D000480:Alkynes; D004952:Esters; D006027:Glycosides