Efficient synthesis of fluorophosphonylated alkyles by ring-opening reaction of cyclic sulfates.
Ring-opening reactions of functionalized 1,2-cyclic sulfates and oxetanes with the phosphonodifluoromethyl carbanion are reported. This approach allows an easy access to fluorinated beta-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nucleoside phosphorylase inhibitors from these alcohols is described.
Diab
Sonia Amel
SA
Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, UMR-CNRS 6507, 6 Bd du Maréchal Juin, 14050 Caen Cedex, France.
Sene
Aboubacary
A
Pfund
Emmanuel
E
Lequeux
Thierry
T
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D004988:Ethers, Cyclic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis*; D013463:Sulfuric Acid Esters / Q000737:chemistry*
D000438:Alcohols; D004988:Ethers, Cyclic; D006845:Hydrocarbons, Fluorinated; D063065:Organophosphonates; D013463:Sulfuric Acid Esters; C005287:oxetane