1228377-14-7

Basic information

• Product Name: C₁₅H₁₆F₃N₃O₈S
• CAS NO: 1228377-14-7
• Molecular Weight: 455.369
• Mol File: 1228377-14-7.mol

Chemical Properties

• CAS DataBase Reference: C₁₅H₁₆F₃N₃O₈S(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₅H₁₆F₃N₃O₈S(1228377-14-7)
• EPA Substance Registry System: C₁₅H₁₆F₃N₃O₈S(1228377-14-7)

Safety Data

• Hazardous Substances Data: 1228377-14-7(Hazardous Substances Data)

Upstream product

• 117139-96-5 (2S)-2-[(2-nitrobenzene)sulfonamido]propanoic acid 
• 1228376-90-6 (2R,4S)-2-trifluoromethyloxazolidine-4-carboxylic acid methyl ester 

Relevant articles and documents

Conformational properties of peptides incorporating a fluorinated pseudoproline residue

We have recently reported the synthesis of enantiomerically pure CF 3-oxazolidine pseudoprolines (CF3-ΨPro). Complete NMR studies, together with DFT calculations, have highlighted the marked stereoelectronic effects of the CF3 group on these new proline surrogates. In this paper, we describe for the first time the conformational features of dipeptides incorporating one CF3-ΨPro residue. Extensive NMR analyses have been carried out in solution and revealed the presence of a stable type-VI β-turn in a pseudotetrapeptide sequence.

Incorporation of CF3-pseudoprolines into peptides: A methodological study

The peptide coupling reactions allowing the incorporation of trifluoromethyl substituted oxazolidine-type pseudoprolines (CF 3-ΨPro) into peptide chains have been studied. While standard protocols can be used for the peptide coupling reaction at the C-terminal position of the CF3-ΨPro, acid chloride activation has to be used for the peptide coupling reaction at the N-terminal position to overcome the decrease of nucleophilicity of the CF3-ΨPro. We demonstrate that the N-amidification of a diastereomeric mixture of CF3-ΨPro using Fmoc-protected amino acid chloride without base gave the corresponding dipeptides as a single diastereomer (6 examples). The ratio of the cis and trans amide bond conformers was determined by NMR study, highlighting the role of the Xaa side chains in the control of the peptide backbone conformation. Finally a tripeptide bearing a central CF3-ΨPro has been successfully synthesized.

Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines

Trifluoromethyl group containing oxazolidines (Fox) are conveniently synthesized by condensation of serine esters with trifluoroacetaldehyde hemiacetal or trifluoroacetone. These oxazolidines can undergo N-acylation and amidification reactions and are com