@article { ISI:000272083700044, title = {Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters}, journal = {Journal of Organic Chemistry}, volume = {74}, number = {23}, year = {2009}, month = {DEC}, pages = {9233-9236}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, 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.

}, issn = {0022-3263}, doi = {10.1021/jo901837z}, author = {Vidadala, Srinivasa Rao and Thadke, Shivaji A. and Hotha, Srinivas} }