Pentafluorophenyl Sulfonate Ester as a Protecting Group.
Pentafluorophenol and its derivatives are widely used for making polymers, with unique properties, synthesis of aminoacids, peptides and nucleosides, which are the intermediates in synthesis of antitumor agents, HIV inhibitors (2-4), as components of metallocene catalysis systems for olefin polymerization.The synthesis and polymerization of two new vinyl monomers, pentafluorophenyl vinyl ether and 1,2-difluorovinyl pentafluorophenyl ether, are also presented. Key Words: Ethers, pentafluorophenyl, pentafluorophenoxy, alkyl, vinyl, difluorovinyl, polymer-ization, and pyrolysis. 1. Introduction In a previous report (I),2 we have described the.About Pentafluorophenol Pentafluorophenol is a fluorobenzene derivative primarily used to promote coupling to carboxylic and sulfonic acids by activation as a pentafluorophenyl ester. The strong electron-withdrawing character of the 5 fluorine atoms on the benzene ring makes the pentafluorophenolate anion an especially good leaving group.
Searching the literature we found references to the p-nitrophenyl esters of isonicotinic (2,3) and picolinic acid (2,3,4), which have been used for the synthesis of potent antagonists of the luteinizing hormone-releasing hormone (LHRH) (4,5).The only other ester reported was the pentachlorophenyl ester of isonicotinic acid (), however in the latter case, no experimental details were given.The application of fluorenylmethoxycarbonyl-amino-acid pentafluorophenyl esters to solid phase peptide synthesis under polar reaction conditions is described. Reaction rates are increased in the presence of l-hydroxybenzotriazole. The technique is illustrated by preparation of decapeptide and dodecapeptide sequences. Previous article in issue.
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