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Chemical Compound Review:

Triflat trifluoromethanesulfonate

Synonyms: TfO(-), CHEBI:48547, AC1MBZ4O, CF3SO3(-), Trifluormethansulfonat, ...

This record was replaced with 62406.

Gruber, P.R. et al., Seward, C. et al., Mong, T.K. et al., Snyder, S.E. et al., Nomizu, M. et al., et al.

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Psychiatry related information on trifluoromethanesulfonic acid

In addition, using the promoter system 1-(benzensulfinyl)piperidinetrifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimidetrifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems [1].

High impact information on trifluoromethanesulfonic acid

Key steps of this approach to 1 involve a siloxy-epoxide semipinacol rearrangement of 5 to 6, a B-alkyl Suzuki-Miyaura coupling reaction by using enol trifluoromethanesulfonate 19 and a substrate-directed hydrogenation reaction of 24 [2].
[reaction: see text] Treatment of sarcophytoxide with trimethylsilyl trifluoromethanesulfonate afforded an aromatic ketone as an unusual cyclization product [3].
We have studied interhalogen/silver trifluoromethanesulfonate (IX/AgOTf) promoted glycosylations and found differences in the sensitivity of the formed oxocarbenium ions (e.g. from compounds with or without participating groups) toward halide nucleophiles [4].
1-Heptyl-4-(butyl-4-sulfonic acid) triazolium trifluoromethanesulfonate, 6b, in its role as a Brønsted acid, is an effective solvent/catalyst for high yield esterification and hetero-Michael addition reactions and may be recycled for repetitive use [5].
The reaction of AgX, where X = trifluoroacetate (CF(3)CO(2)(-), tfa), nitrate (NO(3)(-)), trifluoromethanesulfonate (triflate, CF(3)SO(3)(-), OTf), hexafluorophosphate (PF(6)(-)), or perchlorate (ClO(4)(-)), with 2,2',3' '-tripyridylamine (tpa) yields five novel silver(I) complexes, which have been structurally characterized [6].

Biological context of trifluoromethanesulfonic acid

Another reagent, 1,4,6-trimethyl-2-vinylpyridinium trifluoromethanesulfonate, directly eliminates interference due to sample mercaptans such as glutathione by means of a very fast alkylation reaction [7].
Reductive cleavage of the fully methylated polysaccharide in the presence of triethylsilane and trimethylsilyl trifluoromethanesulfonate and subsequent acetylation in situ gave six partially methylated 1,4-anhydroalditol acetates as the major products and three partially methylated 1,5-anhydroalditol acetates as minor products [8].

Anatomical context of trifluoromethanesulfonic acid

Studies on peptides. CXLVIII. Application of a new deprotecting procedure with trimethylsilyl trifluoromethanesulfonate for the syntheses of two porcine spinal cord peptides, neuromedin U-8 and neuromedin U-25 [9].

Associations of trifluoromethanesulfonic acid with other chemical compounds

Samples were then derivatized with 4'-bromophenacyl trifluoromethanesulfonate for spectrophotometric detection or 2-(2,3-naphthalimino)ethyl trifluoromethanesulfonate for fluorescence detection and quantified by high-performance liquid chromatography [10].
A substrate-unspecified glycosylation reaction promoted by copper(II) trifluoromethanesulfonate in benzotrifluoride [11].
Compounds 1 and 3 were condensed under the conditions of base-deficient, silver trifluoromethanesulfonate-mediated glycosylation to give a fully protected rhamnobioside, which on O-debromoacetylation afforded the disaccharide nucleophile 10 [12].
Glycosylation with an ortho ester from d-maltose was performed successfully at room temperature in dichloromethane in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst [13].
Reaction of the free base form of PHP with [11C]methyl trifluoromethanesulfonate at room temperature in N,N-dimethylformamide, followed by high performance liquid chromatography (HPLC) purification, provided [11C]PMP in 57% radiochemical yield, > 99% radiochemical purity, and > 1500 Ci/mmol at the end of synthesis [14].

Gene context of trifluoromethanesulfonic acid

Application of the trimethylsilyl trifluoromethanesulfonate deprotecting procedure for the synthesis of porcine peptide YY (PYY) [15].
For alternative synthesis of pET-39, the use of trimethylsilyl trifluoromethanesulfonate for the removal of peptide from the resin generated a major side product, which was characterized. hET-38 was found to be less effective in vitro, when compared to endothelin [16].

Analytical, diagnostic and therapeutic context of trifluoromethanesulfonic acid

Potentiometric titrations were conducted at temperatures of 10, 25, and 50 degrees C and ionic strengths of approximately 0.3, 0.5, and 1.0 molal in aqueous solutions of the inert 1:1 electrolyte sodium trifluoromethanesulfonate (NaTr) [17].

References

Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small-cell lung cancer. Mong, T.K., Lee, H.K., Duron, S.G., Wong, C.H. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
An asymmetric formal synthesis of fasicularin. Fenster, M.D., Dake, G.R. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
Unusual transannular cyclization products of sarcophytoxide, a 14-membered marine cembranoid: anomalous stereochemistry of epoxide-ketone rearrangement. Nii, K., Tagami, K., Matsuoka, K., Munakata, T., Ooi, T., Kusumi, T. Org. Lett. (2006) [Pubmed]
Study of interhalogens/silver trifluoromethanesulfonate as promoter systems for high-yielding sialylations. Meijer, A., Ellervik, U. J. Org. Chem. (2002) [Pubmed]
Low melting N-4-functionalized-1-alkyl or polyfluoroalkyl-1,2,4-triazolium salts. Mirzaei, Y.R., Xue, H., Shreeve, J.M. Inorganic chemistry. (2004) [Pubmed]
Anion dependent structures of luminescent silver(i) complexes. Seward, C., Chan, J., Song, D., Wang, S. Inorganic chemistry. (2003) [Pubmed]
Spectrophotometric assay of superoxide dismutase activity based on the activated autoxidation of a tetracyclic catechol. Nebot, C., Moutet, M., Huet, P., Xu, J.Z., Yadan, J.C., Chaudiere, J. Anal. Biochem. (1993) [Pubmed]
Isolation and analysis by the reductive-cleavage method of linkage positions and ring forms in the Mycobacterium smegmatis cell-wall arabinogalactan. Gruber, P.R., Gray, G.R. Carbohydr. Res. (1990) [Pubmed]
Studies on peptides. CXLVIII. Application of a new deprotecting procedure with trimethylsilyl trifluoromethanesulfonate for the syntheses of two porcine spinal cord peptides, neuromedin U-8 and neuromedin U-25. Fujii, N., Ikemura, O., Funakoshi, S., Matsuo, H., Segawa, T., Nakata, Y., Inoue, A., Yajima, H. Chem. Pharm. Bull. (1987) [Pubmed]
Quantification of carnitine, acetylcarnitine, and total carnitine in tissues by high-performance liquid chromatography: the effect of exercise on carnitine homeostasis in man. Minkler, P.E., Brass, E.P., Hiatt, W.R., Ingalls, S.T., Hoppel, C.L. Anal. Biochem. (1995) [Pubmed]
A substrate-unspecified glycosylation reaction promoted by copper(II) trifluoromethanesulfonate in benzotrifluoride. Yamada, H., Hayashi, T. Carbohydr. Res. (2002) [Pubmed]
Stereoselective syntheses of a di-, tri-, and tetra-saccharide fragment of Shigella dysenteriae type 1 O-antigen using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride as a glycosyl donor. Pavliak, V., Kovác, P., Glaudemans, C.P. Carbohydr. Res. (1992) [Pubmed]
Nonnatural branched polysaccharides: synthesis and properties of chitin and chitosan having disaccharide maltose branches. Kurita, K., Akao, H., Yang, J., Shimojoh, M. Biomacromolecules (2003) [Pubmed]
Synthesis of 1-[11C]methylpiperidin-4-yl propionate ([11C]PMP) for in vivo measurements of acetylcholinesterase activity. Snyder, S.E., Tluczek, L., Jewett, D.M., Nguyen, T.B., Kuhl, D.E., Kilbourn, M.R. Nucl. Med. Biol. (1998) [Pubmed]
Application of the trimethylsilyl trifluoromethanesulfonate deprotecting procedure for the synthesis of porcine peptide YY (PYY). Ono, S., Kiyama, S., Kitagawa, K., Futaki, S., Nakamura, T., Taike, T., Akita, T., Sumi, S., Inoue, K., Fujimura, M. Int. J. Pept. Protein Res. (1989) [Pubmed]
Solid phase peptide synthesis of human endothelin precursor peptides using two-step hard acid deprotection/cleavage methods. Nomizu, M., Inagaki, Y., Iwamatsu, A., Kashiwabara, T., Ohta, H., Morita, A., Nishikori, K., Otaka, A., Fujii, N., Roller, P.P. Int. J. Pept. Protein Res. (1991) [Pubmed]
Formation quotients of aluminum sulfate complexes in NaCF3SO3 media at 10, 25, and 50 degrees C from potentiometric titrations using a mercury/mercurous sulfate electrode concentration cell. Xiao, C., Wesolowski, D.J., Palmer, D.A. Environ. Sci. Technol. (2002) [Pubmed]

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