Glycosylation of 2-(2-Propylsulfinyl)benzyl 1,2-Orthoester Glycosides Initiated by Sulfoxide Activation.

ABSTRACT

We have developed a highly effective glycosylation method that involves the activation of 2-(2-propylsulfinyl)benzyl 1,2-orthoester glycosides using triflic anhydride (Tf2O). Our research indicates that half of the glycosyl donor is activated through Tf2O via an interrupted Pummerer reaction mechanism, while the remaining portion is activated by triflic acid (TfOH) generated in situ. As a result, as little as 0.5 equiv of Tf2O is adequate for activating the orthoester glycoside donors. This glycosylation procedure offers several benefits, such as high efficiency, wide applicability, and the utilization of a recyclable leaving group.