157337-07-0Relevant academic research and scientific papers
Diastereotopic fluorine substituents as 19F NMR probes of screw-sense preference in helical foldamers
Pike, Sarah J.,De Poli, Matteo,Zawodny, Wojciech,Raftery, James,Webb, Simon J.,Clayden, Jonathan
, p. 3168 - 3176 (2013/06/04)
Ligating simple amino alcohol or amino ester monomers containing enantiotopic fluorine substituents to the C-terminus of a helical peptide places the fluorine atoms in diastereotopic environments, and gives two distinct and easily identifiable signals in the 19F NMR spectrum. In the case of a dynamically inverting helix built from achiral monomers, the chemical shift separation between the 19F signals provides a simple means of analysing the ratio of screw-sense conformers in the oligomer, in cases where an asymmetric bias leads to a screw-sense preference. The Royal Society of Chemistry 2013.
Synthesis of methyl 2-(fluoromethyl)-3-fluoroalanine
Davis,Reddy,Bental,Deutsch
, p. 701 - 702 (2007/10/02)
The title compound 1b, an important intracellular pH indicator, is conveniently prepared in 44% overall yield from 1,3-difluoro-2-propanol (2). Key steps in this synthesis include oxidation of 2 to 1,3-difluoroacetone (3) in near quantitative yield using KMnO4/CuSO4 and the addition of trimethylsilyl cyanide to a phenyl glycinol protected imine. The efficiency of this process was enhanced further by use of crude reaction mixtures of their solutions.
