We have developed a highly effective glycosylation method that involves the activation of 2-(2-propylsulfinyl)benzyl 1,2-orthoester glycosides using triflic anhydride (TfO). Our research indicates that half of the glycosyl donor is activated through TfO via an interrupted Pummerer reaction mechanism, while the remaining portion is activated by triflic acid (TfOH) generated . As a result, as little as 0.5 equiv of TfO 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.
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| http://dx.doi.org/10.1021/acs.orglett.4c02210 | DOI Listing |
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