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