Tressler, Caitlin M.; Zondlo, Neal J. published their research in Organic Letters on December 16 ,2016. The article was titled 《Synthesis of Perfluoro-tert-butyl Tyrosine, for Application in 19F NMR, via a Diazonium-Coupling Reaction》.Formula: C24H22N2O4 The article contains the following contents:
A practical synthesis of the novel highly fluorinated amino acid Fmoc-perfluoro-tert-Bu tyrosine was developed. The sequence proceeds in two steps from com. available Fmoc-4-NH2-phenylalanine via diazotization followed by diazonium coupling reaction with perfluoro-tert-butanol. In peptides, perfluoro-tert-Bu tyrosine was detected in 30 s by NMR spectroscopy at 500 nM peptide concentration due to nine chem. equivalent fluorines that are a sharp singlet by 19F NMR. Perfluoro-tert-Bu ether has an estimated σp Hammett substituent constant of +0.30. In addition to this study using Fmoc-D-Phe(4-NH2)-OH, there are many other studies that have used Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2Formula: C24H22N2O4) was used in this study.
Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2) belongs to ethers.The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes. Formula: C24H22N2O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem