Synthesis of isomerically pure carboxylate- and sulfonate-substituted xanthene fluorophores

Woodroofe, Carolyn C.; Lim, Mi Hee; Bu, Weiming; Lippard, Stephen J.

doi:10.1016/j.tet.2005.01.024

Cited by 45 publications

(34 citation statements)

References 20 publications

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“…Subsequent hydrolysis under strong alkaline conditions followed by acidification yielded the desired benzophenones 5 and 6. [7] The key step to pure regioisomers of 5-and 6-carboxyfluoresceins (8 and 7) is the separation of benzophenones 5 and 6. Benzophenone 6 forms a 4:1 arrangement with MeOH in the crystal structure after crystallization from MeOH/H 2 O (see Figure S2 in the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[6] Other regioisomeric fluorescein derivatives have also been separated. [7][8][9] To the best of our knowledge, a large-scale synthesis of 100 % regioisomeric pure 5-and 6-carboxyfluorescein without chromatographic purification has never been reported. Carboxyfluoresceins are widely used as fluorescent-labeling reagents by esterification or amidation at the 5-or 6-position.…”

Section: Introductionmentioning

confidence: 99%

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Facile Large‐Scale Synthesis of 5‐ and 6‐Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes

et al. 2015

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A series of fluorescein dyes have been prepared from a common precursor through a very simple synthetic procedure, giving access to important precursors for fluorescent probes. The method has proven an efficient access to regioisomerically pure 5‐ and 6‐carboxyfluoresceins on a large scale, in good yields, and with high regioisomeric purity. Furthermore, we have applied the method to the development of a new type of mixed fluorescein derivatives of 5‐carboxyfluorescein. We have demonstrated the scope of the procedure by synthesizing a new type of double chromophore within the fluoro‐Jade family.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile Large‐Scale Synthesis of 5‐ and 6‐Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes

et al. 2015

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“…Fluorescein and phenolphthalein can be synthesized from phthalic anhydride with resorcinol or phenol by acid catalyzed Friedel-Crafts acylations 13) . In these reactions, the addition of resorcinol or phenol occurs at one carbonyl group of phthalic anhydride.…”

Section: Resultsmentioning

confidence: 99%

Friedel-Crafts Acylation of Anisole with Phthalic Anhydride Catalyzed by Solid Superacid of Sulfated Zirconia

Nakamura

Tanaka

Matsuhashi

2010

J. Jpn. Petrol. Inst.

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Friedel-Crafts acylation of anisole with phthalic anhydride was performed over several types of sulfated zirconia catalysts prepared from zirconia gel, JRC-ZRO-2, JRO-ZRO-3, JRC-ZRO-4, and JRO-ZRO-5, which are reference catalysts supplied by the Reference Catalyst Committee of the Catalysis Society of Japan, by equilibrium adsorption method and the kneading method. The only product was the diacylated product C6H4[CO(C6H4OCH3)]2; no monoacylated product, C6H4[CO(C6H4OCH3)]COOH, was observed. However, a large amount of monoacylated product was obtained when the acylation was catalyzed by the dissolved AlCl3. Phthalic acid monoethyl ester was produced by posttreatment of the catalyst with ethanol. Reaction time and temperature had little effect on the yield of ethyl ester. The diacylated product is probably formed by the addition of two anisoles to one carbonyl group in phthalic anhydride with subsequent rearrangement of the anisole group to the carbon of the other carbonyl group, because the other carbonyl group on phthalic anhydride is likely to be activated on the surface of the superacid. Observations with various solid superacid catalysts indicated the superacid sites on the surface are required for the formation of diacylated product.

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“…As none of the tested compounds appeared to have significant activity (see below), the separation was definitively not carried out although some recrystallization protocols have been described in which protection deprotection steps were required. 40,[44][45][46] The last step of the synthesis consists in the insertion of iodine in the xanthene moiety. Among the different classical methodologies, we have selected one of the smoothest (I 2 /HIO 3 in EtOH).…”

Section: Chemistrymentioning

confidence: 99%

Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

Pietrancosta

Kessler

Favre-Besse

et al. 2010

Bioorganic & Medicinal Chemistry

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Synthesis of isomerically pure carboxylate- and sulfonate-substituted xanthene fluorophores

Cited by 45 publications

References 20 publications

Facile Large‐Scale Synthesis of 5‐ and 6‐Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes

Facile Large‐Scale Synthesis of 5‐ and 6‐Carboxyfluoresceins: Application for the Preparation of New Fluorescent Dyes

Friedel-Crafts Acylation of Anisole with Phthalic Anhydride Catalyzed by Solid Superacid of Sulfated Zirconia

Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

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