317845-13-9Relevant academic research and scientific papers
New stereoconservative syntheses of β,β,β- and γ,γ,γ-trifluoro-α-amino, α-hydroxy, and α-mercapto acids and their incorporation into a peptide and depsipeptide fragment
Schedel,Dmowski,Burger
, p. 1681 - 1688 (2007/10/03)
Syntheses of β,β,β- and γ,γ,γ-trifluoro-α-amino, α-hydroxy and a-mercapto acids using hexafluoroacetone as protecting and activating reagent are described. The key step of the syntheses is the transformation of an ω-carboxy group into a trifluoromethyl group on treatment with sulfur tetrafluoride. The carboxy activated species obtained are suitable for direct incorporation into peptide and depsipeptide fragments. RP-HPLC experiments and Mosher's TMPA method (1H and 19F) demonstrate that the reaction sequence occurs without racemization.
