Abstract
In our previous research on the synthesis of 3,5-di-O-benzoyl-2-C-methyl-d-arabino-γ-lactone 4a, the reaction mechanism of DMSO-mediated configuration inversion of C2 hydroxyl group in the lactone was ambiguous. As a follow-up to this research, we used 18O-labelled H2O and DMSO to investigate the mechanism. It was surprisingly discovered that DMSO served as an oxygen donor to stereoselectively displace the leaving group, and was regenerated in the reaction. The protecting groups had no influence on the inversion, but would significantly affect the yield. We also disclosed another approach for the synthesis of 4a without using the expensive Tf2O, which was more suitable for application.
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