A convenient and efficient approach was developed to synthesize α-Kdo -glycosides based on the TfO/(-Tol)SO preactivation strategy using peracetylated Kdo thioglycoside as a donor. Under the optimized reaction conditions, several -glycoside products, including α-(2 → 1)-, α-(2 → 2)-, α-(2 → 3)-, and α-(2 → 6)-Kdo products, were stereoselectively synthesized in high yields. Remarkably, a series of aromatic α-Kdo -glycosides were first and successfully constructed in high yields. An S2-like mechanism was revealed by DFT calculations and experimental results.
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