Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues.
Enantioenriched tetrafluorinated aryl-C-nucleosides were synthesised in four steps from 1-benzyloxy-4-bromo-3,3,4,4-tetrafluorobutan-2-ol. The presence of the tetrafluorinated ethylene group is compatible with O-phosphorylation of the primary alcohol, as demonstrated by the successful preparation of the tetrafluorinated naphthyl-C-nucleotide.
Bonnac
Laurent
L
University of Oxford, Chemistry Research Laboratory, Oxford, United Kingdom OX1 3TA.
Lee
Sarah E
SE
Giuffredi
Guy T
GT
Elphick
Lucy M
LM
Anderson
Alexandra A
AA
Child
Emma S
ES
Mann
David J
DJ
Gouverneur
Véronique
V
D000440:Butanols / Q000737:chemistry; D054879:Halogenation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010766:Phosphorylation; D013237:Stereoisomerism; D013379:Substrate Specificity
D000440:Butanols; D009705:Nucleosides; D010100:Oxygen