Nucleotides and nucleic acids: a source of inspiration for the development of new, phosphorus-centered functional groups.
Synthetic methodologies aiming at the creation of new phosphorus-centered functional groups are reported, as well as applications to the field of nucleotide chemistry. Thus, difluorophosphonothioate-based, ionic reagents 3b and 3d are shown to allow the stereocontrolled and efficient synthesis of phosphonodifluoromethyl analogues of nucleoside-3'-phosphates. An alternate, radical approach describes the use of hypophosphorous acid to stereoselectively link two furanosyl units in positions 3 and 5, and to provide an access to alpha,alpha-difluoro-H-phosphinates. These intermediates are shown to be precursors to the corresponding fluorinated phosphonic acids, phosphonothioic acids and variously substituted phosphinates.
Lopin
Chrystel
C
University of Rouen, Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, IRCOF, rue Tesnières, Mont Saint Aignan, France.
Garipova
Goulnara
G
Kalinina
Irina
I
Raboisson
Pierre
P
Osaki
Tomohisa
T
Gautier
Arnaud
A
Balieu
Sébastien
S
Salcedo
Carmen
C
Gouhier
Géraldine
G
Piettre
Serge R
SR
D009696:Nucleic Acids / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry; D013237:Stereoisomerism
D009696:Nucleic Acids; D009711:Nucleotides; D010755:Organophosphates; D010721:Phosphinic Acids