- A fluorocarbon nucleoamphiphile for the construction of actinide loaded microspheres
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The synthesis of a novel fluorocarbon based nucleoamphiphile; 2′,3′-O-di-2H,2H,3H,3H-perfluoro-undecanoyl-uridine-5′ -phosphocholine (DiF17UPC) is described. DiF17UPC self-assembles into lamellar organizations unlike 1,2-distearoyluridinophosphocholine (DSUPC) which forms DNA-like helical fibre under similar conditions. The fluorocarbon chains have a significant impact on the supramolecular assemblies formed by the nucleoamphiphiles. The SEM and TEM images collected clearly indicate the formation of microspheres when DiF17UPC is hydrated in the presence of thorium nitrate at high temperature (T > 90 °C). The DiF17UPC/Th4+ microspheres vary in size from 0.5 to 12 μm.
- Moreau, Louis,Campins, Nathalie,Grinstaff, Mark W.,Barthélémy, Philippe
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- Fluorous oligosaccharide synthesis using a novel fluorous protective group
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equation presented The Bfp (bisfluorous chain type propanoyl) group, a novel fluorous protecting reagent, was able to be prepared easily. The Bfp group was readily introduced to carbohydrate, was removed in high yield, and was recyclable after cleavage. Use of the Bfp group made it possible to synthesize a tetrasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified by using only simple fluorous-organic solvent extraction and was monitored by NMR, mass spectroscopy, and TLC.
- Miura, Tsuyoshi,Hirose, Yuriko,Ohmae, Masashi,Inazu, Toshiyuki
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- Fluorous derivatives of (1R,2R)-diaminocyclohexane as chiral ligands for metal-catalyzed asymmetric reactions
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Perfluoroalkyl-substituted, enantiopure diamines derived from (1R,2R)-diaminocyclohexane were conveniently prepared from readily available precursors. In situ generated metal complexes of these ligands were tested as chiral catalysts in three standard asymmetric reactions (cyclopropanation of styrene, hydrogen transfer reduction of acetophenone, and allylic alkylation of 1,3-diphenyl-2-propenyl acetate) affording enantioselectivities of up to 47% in the copper-catalyzed cyclopropanation of styrene.
- Bayardon, Jerome,Sinou, Denis,Holczknecht, Orsolya,Mercs, Laszlo,Pozzi, Gianluca
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- Philic and phobic segregation in liquid-crystal ionic dendrimers: An enthalpy-entropy competition
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(Figure Presented) A molecular tug of war between non- and semifluorinated alkyl chains (see picture) occurs when they are forced together by ionic attachment to a poly(propylene imine) dendrimer. Unexpected mesomorphic properties appear as a consequence of the competition of both substituents to control the supramolecular organization of the molecules.
- Hernandez-Ainsa, Silvia,Marcos, Mercedes,Barbera, Joaquin,Serrano, Jose L.
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- FLUOROUS COMPOUND, METHOD OF PREPARING FLUOROUS TAGGED PROTEIN, AND METHOD OF IMMOBILIZING PROTEIN
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A fluorous compound, a method of preparing a fluorous tagged protein, and a method of immobilizing protein are provided. The fluorous compound is represented by Y-L-R, wherein Y is a fluorous group; L is a linker, and the linker includes a bivalent group having a sulfo group, a bivalent group having a carboxyl group, or a bivalent group of hydrophilic amino acid; and R is a functional group capable of bonding to protein.
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Paragraph 0074-0075
(2019/01/06)
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- Synthesis and surface properties of new semi-fluorinated sulfobetaines potentially usable for 2D-electrophoresis
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New semi-fluorinated amidosulfobetaines, homologs of hydrocarbon amidosulfobetaines (ASB) commonly used in two-dimensional gel electrophoresis (2DE), were prepared in three steps from 2-F-alkylethyl iodide or F-alkyl iodide. Their synthesis was described and their air-water interface properties were investigated and compared with their perhydrogenated counterpart properties. The influence of the relative lengths of the perfluorinated and hydocarbonated moieties was discussed. 2DE of a rat testicular membrane fraction was performed comparatively using one of these fluorinated sulfobetaines and its hydrocarbon homolog; these preliminary results showed the great potential of the semi-fluorinated sulfobetaines in proteomic analysis.
- Thebault, Pascal,Taffin de Givenchy, Elisabeth,Starita-Geribaldi, Mireille,Guittard, Frederic,Geribaldi, Serge
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p. 211 - 218
(2008/03/13)
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- Synthesis and surface antimicrobial activity of a novel perfluorooctylated quaternary ammonium silane coupling agent
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A novel perfluorooctyl-containing quaternary ammonium salt was designed and synthesized, which was applied as a surface modification agent to provide the treated cotton fabrics with antimicrobial activity and low critical surface energy.
- Shao, Hui,Meng, Wei-Dong,Qing, Feng-Ling
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p. 721 - 724
(2007/10/03)
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- Rapid oligosaccharide synthesis using a fluorous protective group
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The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.
- Miura, Tsuyoshi,Goto, Kohtaro,Waragai, Hideki,Matsumoto, Hiroharu,Hirose, Yuriko,Ohmae, Masashi,Ishida, Hide-Ki,Satoh, Ai,Inazu, Toshiyuki
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p. 5348 - 5353
(2007/10/03)
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- Combining lipase-catalyzed enantiomer-selective acylation with fluorous phase labeling: A new method for the resolution of racemic alcohols
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Lipase-catalyzed acylation of racemic alcohols with a highly fluorinated acyl donor allows their kinetic resolution accompanied by the simultaneous enantiomer-selective fluorous phase labeling. Both the tagged and the untagged enantiomer can be separated without chromatography by a very efficient partition between a fluorous and an organic phase. The method has been successfully applied to the resolution of typically racemic secondary alcohols of low molecular weight. The fluorous label can be recovered quantitatively.
- Hungerhoff, Benno,Sonnenschein, Helmut,Theil, Fritz
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p. 1781 - 1785
(2007/10/03)
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- Synthese des isocyanates de 2-F-alkylethyle
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Isocyanates are extremely important compounds in organic synthesis but their preparation is not always easy.One of the most convenient methods uses the acids as intermediates.In the F-alkyl series it is sometimes difficult to obtain them.We have optimized an efficient synthetic route to 2-F-alkylethyl isocyanates.
- Jouani, A. M.,Szoenyi, F.,Cambon, A.
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- CARBONYLATION OF 1-PERFLUOROALKYL-SUBSTITUTED 2-IODOALKANES CATALYZED BY TRANSITION-METAL COMPLEXES
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Carboxylic acids and esters with perfluoroalkyl substituent at β position were synthesized in good yields from 1-perfluoroalkyl-substituted 2-iodoalkanes and carbon monoxide with water or alcohols in the presence of base by using group VIII transition-metal complexes as catalysts.
- Urata, Hisao,Kosukegawa, Osamu,Ishii, Yoshimitsu,Yugary, Hideki,Fuchikami, Takamasa
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p. 4403 - 4406
(2007/10/02)
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- PALLADIUM-CATALYZED DOUBLE CARBONYLATION OF ALKYL IODIDES BEARING PERFLUOROALKYL GROUP
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Double carbonylation of 1-perfluoroalkyl substituted 2-iodoalkanes are effectively catalyzed by palladium complexes in the presence of primary or secondary amines leading to the formation of the corresponding α-keto amides in good yields.
- Urata, Hisao,Ishii, Yoshimitsu,Fuchikami, Takamasa
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p. 4407 - 4410
(2007/10/02)
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