307501-98-0

Upstream product

• 82113-65-3 bis(trifluoromethanesulfonyl)amide 
• 100422-04-6 (2,2,2-trifluoroethyl)-λ³-iodanediyl bis(2,2,2-trifluoroacetate) 
• 71-43-2 benzene 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 

Downstream Products

• 303049-60-7 N^α-2,2,2-trifluoroethylphenylalanine tert-butyl ester 

Relevant academic research and scientific papers

Easy preparation of bioactive peptides from the novel Nα-trifluoroethyl amino acids

Nα-Trifluoroethyl amino acids have been prepared for the first time and unexpectedly found to behave as conventionally N-protected amino acids. Novel unnatural peptides are easily prepared in high yields without racemization. The observed chemistry results from steric factors as well as from the acidity of the CF3CH2NH group, according to comparative experiments. Of ten dipeptides that were tested for antitumor activity, CF3CH2-L-Tyr-L-Ile-OtBu was the most active.

Synthesis and structure of novel perfluorinated iodinanes

Several novel iodinanes have been prepared and structurally characterized. The structures of all are heavily influenced by secondary bonding involving the iodine(III) center and oxygen or chlorine. The iodonium salt, [Ph(CF3CH2)I]CF3SO2NSO2CF3, has a chain structure with the anion in a transoid conformation, while the diphenyl derivative, [Ph2I]CF3SO2NSO2CF3, forms a dimeric structure which stabilizes a cisoid conformation of the anion. In comparison to the known compound, PhICl2, which has a simple chain structure, perfluoroalkyliodinedichlorides CF3CH2ICl2 and CHF2(CF2)5CH2ICl2, have more complicated structures in which weak interactions between chains, coupled with aggregation of perfluoro groups, results in the formation of layers. The dicarboxylate, CF3CH2I(O2CCF3)2 has a T-shaped coordination similar to other derivatives, but forms a tetrameric array of molecules not previously seen. (C) 2000 Elsevier Science B.V.

Separable fluorous ionic liquids for the dissolution and saccharification of cellulose

Ionic liquids are an attractive class of solvents for biomass conversion processes. The same properties that make them advantageous - high polarity, water solubility and negligible vapor pressure - hinder their recovery from carbohydrates. We report on th

Syntheses and lipophilicity measurement of Nα/N-terminus-1,1-dihydroperfluoroalkylated α-amino acids and small peptides

(1,1-Dihydroperfluoroalkyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imides (4, n = 0-2) were synthesized and used to transfer the corresponding 1,1-dihydroperfluoroalkyl groups to the α-amino group of (l)tyrosine. The obtained Nα-2,2,2-trifluoroethylated (l)tyrosine (6, n = 0) was further used as the N-terminus in the solid phase peptide synthesis of leucine enkephalin analogue. The lipophilicity of the Nα-1,1-dihydroperfluoroalkylated (l)tyrosines (6, n = 0-2) and N-terminus-2,2,2-trifluoroethylated leucine enkephalin analogue (7), as well as the corresponding parent compounds, was measured.

A discovery tool at work: The unexpected properties of a two-carbon residue

We report the very easy preparation of novel peptides 6a-n as represented by CF3CH2(L)Phe(L)IleOtBu (6a), a prospective antitumor compound. Peptides such as 6a are directly obtained via standard chemistry from a novel class of amino acids, Nα-trifluoroethyl amino acids 4. In fact, unexpectedly, the Nα-1,1,1-trifluoroethyl substitution completely deactivates the α-nitrogen. That is, compounds 4 behave exactly like Nα-protected amino acids, and take part in standard peptide synthesis accordingly. Representative compounds 4a-c are prepared by reaction of commercial amino acid t-butyl esters 2a-c with 1 eq iodonium salt 1 in dichloromethane/water at 22°C in 1 h or less. The reaction is promoted by NaHCO3 (1.5 eq). The intermediate Nα-1,1,1-trifluoroethyl t-butyl esters 3a-c are hydrolyzed and separated from coproducts at the same time by treatment with aqueous HCl at 22°C. Evaporation of the acid extracts provides analytically pure 4a-c in 78-98% yields.