A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography.
Pauff, Steven M.,Miller, Stephen C.
p. 711 - 716
(2013/02/25)
Dynamics for reactions of ion pairs in aqueous solution: Reactivity of tosylate anion ion paired with the highly destabilized 1-(4-methylphenyl)-2,2,2- trifluoroethyl carbocation
The sum of the rate constants for solvolysis and scrambling of carbon bridging and nonbridging oxygen-18 at 4-MeC6H4CH(CF 3)OS(18O2)Tos in 50/50 (v/v) trifluoroethanol/water, (ksolvRki
Teshima, Minami,Tsuji, Yutaka,Richard, John P.
scheme or table
p. 730 - 734
(2011/05/06)
Substituent effects. XX. Highly electron-deficient carbocation solvolyses
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Murata,Sakaguchi,Fujiyama,Mishima,Fujio,Tsuno
p. 1138 - 1145
(2007/10/02)
Solvolysis of 1-Aryl-2,2,2-trifluoroethyl Sulfonates. Kinetic and Stereochemical Effects in the Generation of Highly Electron-Deficient Carbocations
Solvolysis rates of sulfonates XC6H4CH(O3SR)CF3 (R = p-Tol or CF3) correlate with ?+(X) with values of ρ+ between -6.7 and -11.9 depending upon solvent.For the tosylates the rates depend on the solvent parameter YOTs with
Allen, Annette D.,Ambidge, I. Christopher,Che, Claudius,Micheal, Hany,Muir, Ronald J.,Tidwell, Thomas T.
p. 2343 - 2350
(2007/10/02)
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