Phosphorylation of 3',4',5,7-Tetramethyldihydroquercetin

Нифантьев, Э. Е.; Koroteev, M. P.; Kaziev, G. Z.; Koroteev, A. M.; Vasyanina, L. K.; Захарова, И. С.

doi:10.1023/b:rugc.0000018642.90774.a1

Cited by 4 publications

(6 citation statements)

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“…The 13 C NMR spectra of metal complexes IV3VI were assigned on the basis of published data for the free ligands [7,11], acetylacetonate anion [14], and benzoate anion [15].…”

Section: Methodsmentioning

confidence: 99%

“…The 13 C NMR spectra were measured on a Bruker AC-200 spectrometer (50.32 MHz) against external TMS. 2,7,8-Trioxa-1-phosphabicyclo[3,2,1]octane was synthesized according to [7], 1,2-O-isopropylidene-3,5,6-O-phosphinetriyl-a-D-glucofuranose, according to [11], 1,2-O-cyclohexylidene-3,5,6-O-phosphinetriyla-D-glucofuranose, according to [12], and dicarbonylrhodium(I) acetylacetonate, according to [13].…”

Section: Methodsmentioning

confidence: 99%

“…These compounds are available, stable, and exhibit a tendency for coordination with transition metals [6,7].…”

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confidence: 98%

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Rhodium(I) pentasubstituted cationic complexes on the basis of 1,2-O-Alkylidene-3,5,6-O-phosphinetriyl-α-D-glucofuranose

et al. 2004

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Reaction of 1,2-O-alkylidene-a-D-glucofuranose 3,5,6-phosphites with dicarbonylrhodium(I) acetylacetonate was studied. The structure of the reaction products is determined by the reagent ratio. At a 5 : 1 molar ratio, the step ligand-exchange process yields chiral complexes of the [RhL 5 ] + acac ! type. Dynamics of and anion exchange in these complexes are considered.Homoligand cationic complexes of rhodium(I) [RhL 5 ] + X ! have been scarcely explored. They have largely been synthesized on the basis of symmetrical acyclic trialkyl phosphites, as well as carcass phosphorinane3phosphorinane ligands, such as etriol phosphite, metriol phosphite, and adamantyl phosphite [1,2]. Described homoligand cationic rhodium(I) complexes are interesting from the chemical viewpoint. In the solid state they are stable and convenient to operate, and in solutions they undergo fluctuations due to the interconversion of the trigonal bipyramid and distorted tetragonal bipyramid forms [3,4]. It is very important that such complexes can be formed in situ during catalyst formation [5].Here we report on the first synthesis of optically active complexes [RhL 5 ] + X ! on the basis of acac .Rh(CO) 2 as complex-forming agent and unsymmetrical phospholane3phosphorinane systems, such as 1,2-O-isopropylidene-3,5,6-phosphabicyclo-a-Dglucofuranose (I), 1,2-O-cyclohexylidene-3,5,6-phos-ÄÄÄÄÄÄÄÄÄÄÄÄ phabicyclo-a-D-glucofuranose (II), and model 2,7,8-trioxa-1-phosphabicyclo[3,2,1]octane (III), as ligands. These compounds are available, stable, and exhibit a tendency for coordination with transition metals [6,7].Initiating these studies we expected that the ligandexchange reactions of acacRh(CO) 2 with compounds I and II would have certain specific features associated with the large size of the five carbohydratecontaining bicyclophosphite molecules coordinating to one rhodium atom. At the same time, the steric hindrance created by these ligands should not be too strong in view of the fact that the ligated part of the bicyclophosphites is a cone with small O3P3O bond angles. The sums of these angles in ligands I and II are as little as 293o and 295o, respectively [8].

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“…The 13 C NMR spectra of metal complexes IV3VI were assigned on the basis of published data for the free ligands [7,11], acetylacetonate anion [14], and benzoate anion [15].…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Rhodium(I) pentasubstituted cationic complexes on the basis of 1,2-O-Alkylidene-3,5,6-O-phosphinetriyl-α-D-glucofuranose

et al. 2004

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“…

The partially protected quercetin derivatives, viz.

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Phosphorylation of quercetin with trivalent phosphorus reagents

et al. 2004

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Previously we initiated research into phosphorylation of the well-known flavonoid, dihydroquercetin I, with trivalent phosphorus reagents [1,2]. Now we report about the possibility of extending this reaction on quercetin II, a compound that has a more complex structure than flavonoid I.The partially protected quercetin derivatives, viz. quercetin 3,3`,4`,7-tetrabenzylate (III) and 3,3`,4`,7-tetraacetate (IV) contain a free hydroxy group in the C 5 position [3, 4]. Phosphorylation was carried out with 2-chloro-and 2-amido-4,4-dimethyl-1,3,2-dioxaphosphorinanes. The best yields of the target products were achieved when acid chlorides were used. 58 d go E d ; 6 d j R

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“…In continuation of our studies, we examined phospho rylation of new flavonoids, viz., 3 hydroxy (1) and 5,7 di hydroxyflavones (2). The reactions of compounds 1 and 2 with an equimolar amount of hexaethylphosphorous triamide (HEPTA) at room temperature afforded the cor responding diamidophosphites 3 and 4.…”

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confidence: 99%