Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 38, Pages 12778-12787Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302070
Keywords
fluorine; glycomimetics; olefination; radicals; reduction
Categories
Funding
- INSA-ROUEN
- University of Rouen
- Region Haute-Normandie
- Centre National de la Recherche Scientifique (CNRS)
- European Fund for Research Development (EFRD)
- Agence Nationale de la Recherche (ANR)
- LABEX SynOrg
- EFRD [FEDER 43209]
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A new method for the synthesis of fluorinated -C-glycosides is described. The reactions between highly electrophilic radicals (fluorinated or unfluorinated) and a 2-benzyloxyglucal or galactal provide 2-keto-D-arabino- or 2-keto-D-lyxo-hexopyranosides through an addition/fragmentation process. Sodium borohydride mediated or Meerwein-Ponndorf-Verley (MPV) reduction of these compounds provides -C-glycosides that feature appropriate anchoring groups for further synthetic elaboration. The presence of CF(2)CO(2)iPr 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 C-glycosidic analogues of glycoconjugates.
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