Issue 6, 2010

Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues

Abstract

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.

Graphical abstract: Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues

Supplementary files

Article information

Article type
Paper
Submitted
28 Oct 2009
Accepted
05 Dec 2009
First published
25 Jan 2010

Org. Biomol. Chem., 2010,8, 1445-1454

Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues

L. Bonnac, S. E. Lee, G. T. Giuffredi, L. M. Elphick, A. A. Anderson, E. S. Child, D. J. Mann and V. Gouverneur, Org. Biomol. Chem., 2010, 8, 1445 DOI: 10.1039/B922442D

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