Addition of Electrophilic Radicals to 2‐Benzyloxyglycals: Synthesis and Functionalization of Fluorinated α‐C‐Glycosides and Derivatives. Issue 38 (16th August 2013)

• Record Type: Journal Article
• Authors: Colombel, Sophie; Van Hijfte, Nathalie; Poisson, Thomas; Leclerc, Eric; Pannecoucke, Xavier
• Is Part Of: Chemistry. Volume 19:Issue 38(2013)
• Page Start: 12778
• Page End: 12787
• Publication Date: 2013-08-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302070
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new method for the synthesis of fluorinated α‐<italic>C</italic>‐glycosides is described. The reactions between highly electrophilic radicals (fluorinated or unfluorinated) and a 2‐benzyloxyglucal or galactal provide 2‐keto‐<sc>D</sc>‐arabino‐ or 2‐keto‐<sc>D</sc>‐lyxo‐hexopyranosides through an addition/fragmentation process. Sodium borohydride mediated or Meerwein–Ponndorf–Verley (MPV) reduction of these compounds provides α‐<italic>C</italic>‐glycosides that feature appropriate anchoring groups for further synthetic elaboration. The presence of CF₂CO₂<italic>i</italic>Pr or CF₂Br groups at the pseudo‐anomeric position allows efficient reduction/olefination or Br/Li‐exchange/nucleophilic‐addition sequences. These transformations open the way for the synthesis of fluorinated <italic>C</italic>‐glycosidic analogues of glycoconjugates.</p> </abstract>