Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition.
Preparation of several acyclonucleosides containing both a difluoromethylphosphonate group and a triazole moiety is described starting from a difluorophosphonosulfide. The key step of the synthesis involves a copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition between difluorophosphonylated azides and propargylated nucleobases derived from thymine and 2-amino-6-chloropurine.
Diab
Sonia Amel
SA
Laboratoire de Chimie Moléculaire et Thioorganique, ENSICAEN, Université de Caen Basse-Normandie, UMR-CNRS 6507, FR3038, 6 Bd du Maréchal Juin, 14050, Caen Cedex, France.
Hienzch
Antje
A
Lebargy
Cyril
C
Guillarme
Stéphane
S
Pfund
Emmanuel
E
Lequeux
Thierry
T
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*
D000480:Alkynes; D009711:Nucleotides; D063065:Organophosphonates; D003300:Copper