Effect of the size and structure of radicals present in phosphorus esters on the rate of isomerization of these substances

Arbuzov, A. E.; Nesterov, L. V.

doi:10.1007/bf01167811

Cited by 3 publications

(5 citation statements)

References 4 publications

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“…When methyl diphenyl phosphite was used, the reaction proceeded best under vacuum to remove the methyl iodide by-product, which is a reactive electrophile that can consume the phosphite reagent. 14 In seminal studies, Nesterov and Arbuzov have reported that isopropyl diphenyl phosphite is unreactive towards isopropyl iodide at 200 • C, 15 and Golding and co-workers have shown this phosphite is a superior reagent for the Michaelis-Arbuzov reaction with poorly electrophilic 6-iodo galactose derivatives. 14 While Golding and co-workers have reported the synthesis of isopropyl diphenyl phosphite from hexaethylphosphorous triamide, 14, 16 we chose to use hexamethylphosphorous triamide (HMPT) as a more economical starting material.…”

Section: Resultsmentioning

confidence: 99%

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Galactose-derived phosphonate analogues as potential inhibitors of phosphatidylinositol biosynthesis in mycobacteria

et al. 2007

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Galactose-based phosphonate analogues of myo-inositol-1-phosphate and phosphatidylinositol have been synthesized from methyl beta-d-galactopyranoside. Michaelis-Arbuzov reaction of isopropyl diphenyl phosphite or triisopropyl phosphite with a 6-iodo-3,4-isopropylidene galactoside afforded the corresponding phosphonates. Deprotection of the diphenyl phosphonate afforded methyl beta-d-galactoside 6-phosphonate, an analogue of myo-inositol-1-phosphate. The diisopropyl esters of the diisopropyl phosphonate were selectively deprotected and the corresponding anion was coupled with 1,2-dipalmitoyl-sn-glycerol using dicyclohexylcarbodiimide. Deprotection afforded a methyl beta-d-galactoside-derived analogue of phosphatidylinositol. The galactose-derived analogues of phosphatidylinositol and myo-inositol-1-phosphate were not substrates for mycobacterial mannosyltransferases (at concentrations up to 1 mM) involved in phosphatidylinositol mannoside biosynthesis in a cell-free extract of Mycobacterium smegmatis. The galactose-derived phosphonate analogue of phosphatidylinositol was shown to be an inhibitor at 0.01 mM of PimA mannosyltransferase involved in the synthesis of phosphatidylinositol mannoside from phosphatidylinositol, and a weaker inhibitor of the next mannosyltransferase(s), which catalyzes the mannosylation of phosphatidylinositol mannoside.

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Section: Resultsmentioning

confidence: 99%

“…The residue was distilled to afford isopropyl diphenyl phosphite as a colourless liquid (5.13 g, 75%); n 20 D 1.5369 (lit. 15…”

Section: Isopropyl Diphenyl Phosphitementioning

confidence: 99%

Galactose-derived phosphonate analogues as potential inhibitors of phosphatidylinositol biosynthesis in mycobacteria

et al. 2007

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“…Anal. (C5H14N06P) C, , N. Method D. [Hydroxy(4-methoxyphenyl)phosphinyl]acetic Acid (14). A solution of 23.65 g (0.123 mol) of 4-methoxyphenylphosphonous dichloride11 in 25 mL of benzene was added dropwise to a solution of 20 mL of MeOH in 25 mL of benzene cooled in an ice bath.…”

Section: Methodsmentioning

confidence: 99%

“…The preparation of (hydroxyphenylphosphinyl) acetic acid (13) was achieved by the reaction of dimethyl phenylphosphonite with methyl chloroacetate, followed by hydrolysis of the resulting diester with aqueous HC1. When this method was extended to the preparation of [hydroxy(4-methoxyphenyl)phosphinyl] acetic acid (14), the acid hydrolysis of the intermediate diester led to a mixture of two compounds, which from the NMR and TLC data appeared to be the expected product and 1. The preparation of the two target compounds (13 and 14) was accomplished by the method outlined in Scheme IV.…”

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Synthesis and anti-herpes simplex activity of analogs of phosphonoacetic acid

Tr¹,

Js²,

Rr³

et al. 1977

J. Med. Chem.

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The synthesis of monoesters (P and C) of phosphonoacetic acid (PA) is given. The carboxyl esters were prepared by two methods: the reaction of chloroacetates with tris(trimethylsilyl) phosphite, followed by hydrolysis; and by the acid-catalyzed esterification of PA with the appropriate alcohol. P-Monoesters of PA were prepared either by the reaction of alkyl[bis(trimethylsilyl)] phosphite with benzyl chloroacetate followed by deprotection or by the reaction of dimethylphenyl phosphite with benzyl bromoacetate followed by hydrogenolysis. Three aryl- (alkyl-)phosphinic acid derivatives are reported. The above compounds were evaluated for anti-herpes activity against HSV-induced DNA polymerase and in animals infected with herpes dermatitis.

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Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement

Utegenov

Krivykh

Чудин

et al. 2018

Journal of Organometallic Chemistry

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Effect of the size and structure of radicals present in phosphorus esters on the rate of isomerization of these substances

Cited by 3 publications

References 4 publications

Galactose-derived phosphonate analogues as potential inhibitors of phosphatidylinositol biosynthesis in mycobacteria

Galactose-derived phosphonate analogues as potential inhibitors of phosphatidylinositol biosynthesis in mycobacteria

Synthesis and anti-herpes simplex activity of analogs of phosphonoacetic acid

Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement

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