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Molecules 2005, 10(9), 1048-1073; doi:10.3390/10091048

The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates

Laboratoire des Fonctions Azotées et Oxygénées Complexes, IRCOF-Université de Rouen, France
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Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005

Abstract

Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition of phosphorus-centered radicals onto gem–difluoroalkenes or on a process involving the addition of lithiodifluorophosphono- thioates 91 onto a ketone and the subsequent deoxygenation reaction of the adduct. The radical route successfully developed a practical route to α,α–difluoro–H–phosphinates which proved to be useful intermediates to a variety of phosphate isosters. The ionic route led to the first preparation of phosphonodifluoromethyl analogues of nucleoside– 3’–phosphates.
Keywords: Phosphate isoster; difluorophosphonates; difluoro-H-phosphinates; nucleotide analogue; cyclitol analogue. Phosphate isoster; difluorophosphonates; difluoro-H-phosphinates; nucleotide analogue; cyclitol analogue.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Gautier, A.; Lopin, C.; Garipova, G.; Dubert, O.; Kalinina, I.; Salcedo, C.; Balieu, S.; Glatigny, S.; Valnot, J.; Gouhier, G.; Piettre, S. The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates. Molecules 2005, 10, 1048-1073.

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