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 19F NMR active probes for application in structural biology.