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Stereocontrolled Synthesis of 2-Fluorinated C -Glycosides.

A systematic study of the addition of C -based nucleophiles to fluorinated lactones based on 2-deoxy-2-fluoro-d-pyranoses is disclosed. This high yielding, α-selective process was found to be independent on the nature or configuration [( R )-C(sp3 )-F, ( S )-C(sp3 )-F] of the substituent at C2 . Representative, fluorinated analogues of Trehalose, Carminic acid, and the spirocyclic cores of Tofogliflozin and Papulacandin D are also reported. These glycomimics constitute a valuable series of 19 F NMR active probes for application in structural biology.

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