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

Laurent Bonnac; Sarah E. Lee; Guy T. Giuffredi; Lucy M. Elphick; Alexandra A. Anderson; Emma S. Child; David J. Mann; Véronique Gouverneur

doi:10.1039/b922442d

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

Laurent Bonnac, Sarah E. Lee, Guy T. Giuffredi, Lucy M. Elphick, Alexandra A. Anderson, Emma S. Child, David J. Mann, Véronique Gouverneur

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1445-1454
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	6
DOIs	https://doi.org/10.1039/b922442d
State	Published - 2010
Externally published	Yes

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10.1039/b922442d

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title = "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.",

author = "Laurent Bonnac and Lee, {Sarah E.} and Giuffredi, {Guy T.} and Elphick, {Lucy M.} and Anderson, {Alexandra A.} and Child, {Emma S.} and Mann, {David J.} and V{\'e}ronique Gouverneur",

year = "2010",

doi = "10.1039/b922442d",

language = "English (US)",

volume = "8",

pages = "1445--1454",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues

AU - Bonnac, Laurent

AU - Lee, Sarah E.

AU - Giuffredi, Guy T.

AU - Elphick, Lucy M.

AU - Anderson, Alexandra A.

AU - Child, Emma S.

AU - Mann, David J.

AU - Gouverneur, Véronique

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=77749289956&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77749289956&partnerID=8YFLogxK

U2 - 10.1039/b922442d

DO - 10.1039/b922442d

M3 - Article

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AN - SCOPUS:77749289956

SN - 1477-0520

VL - 8

SP - 1445

EP - 1454

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

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

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