Stereoselective Synthesis of β‑C‑Glycosides of 3‑Deoxy‑d-manno-oct-2-ulosonic Acid (Kdo) via SmI2‑Mediated Reformatsky Reactions

An efficient and simple approach for stereoselective synthesis of β-Kdo C-glycosides was described, which relies on easily available peracetylated anomeric acetate or anomeric 2-pyridyl sulfide to couple with carbonyl compounds via SmI2-mediated Reformatsky reactions. The utility of this methodology is exemplified by the streamlined synthesis of a practical β-Kdo C-glycoside with an anomeric aminopropyl linker to conjugate with other biomolecules for further biological studies.