Phosphates 2- phenyl ester

An aromatic phosphate, phenyl ester of phosphoric acid... 

A. Pentoses.—t-Ascorbic acid 2- and 3-phosphates, together with their phosphate esters, give a characteristic colour with ferric chloride and this colour reaction has been used in a study of the hydrolysis of L-ascorbic acid 3-phosphate (58). The acid-catalysed, pseudo-firsi-order hydrolysis proceeds with P—O bond fission, as does the bromine oxidation of its phenyl ester. Both of these observations can be rationalized if (58) is... 

Recently the related cyclization of the phenyl ester of c/j-tetrahydrofuran-3,4-diol monophosphate to the corresponding five-membered phosphate with loss of phenol has been shown to be subject to general catalysis by imidazole132. This reaction serves as a model for the first step in the action of ribonuclease which leads to the formation of the nucleoside 2 ,3 -cyclic phosphate. The actual details of the transition state leading to the cyclic phosphate as catalyzed by the enzyme are presently the subject of some debate. One possibility is the in-line mechanism (53)... 

The 4 -monophosphate was also prepared from the same compound as above (Figure 5). Although the 4 -hydroxyl group in 12 has rather low reactivity, its phosphorylation could be performed with phenyl phosphate and dicyclohexylcarbodiimide (DCC) in pyridine. The reaction product was converted into the benzyl phenyl ester ( ) to facilitate purification. In contrast to the above dibenzyl ester of the glycosyl phosphate, the benzyl phenyl ester of the 4 -phosphate was stable and could be purified by silica gel column chromatography after removal of the propenyl group without decomposition. Hydrogenolytic deprotection of (first with Pd-black then with PtC>2) afforded the 4 -monophosphate 17. 

A comparison of the effect of the structure of phosphate esters on uranium extraction from nitrate media shows that the esters from secondary alcohols give higher uranium distribution coefficients (D s) than those from primary alcohols, phenyl esters extract uranium less strongly than alkyl esters, and benzyl esters are intermediate in extractant strength for uranium (24). 

However, Borden and Smithi have found that treatment of the p-nitro-phenyl esters of 2 -deoxyribonucleoside 3 - and 5 -phosphates and of ribo-nucleoside 5 -phosphates with potassium fert-butoxide in methyl sulfoxide affords the corresponding nucleoside 3 5 -cyclic phosphates in excellent yields. Other phosphorus-activated nucleotides, such as nucleoside 5 -phosphorofluoridates, 5 -(2,4-dinitrophenyl phosphate)s and 5 -(PS-P " diphenyl pyrophosphate) s, were also cyclized to nucleoside 3 5 -cyclic... 

The structures of 1,3,2-dioxaphosphinanes of biochemical significance to have been solved by x-ray crystallography are numerous the phenyl ester of thymidine 3, 5 -cyclic phosphate is an example <75PNA(72)1335, 87JA4058>. In the 1,3,5-dioxaphosphinane series, conformational studies by NMR have been supported by x-ray crystal structures <87IZV418>. 

The tricresyl phosphate of commerce is not a pure substance, being in part made up of the mixed cresyl-phenyl esters. Also, Bieber, Klaus and Tewksbury [41] showed that in addition to about 0.3 weight-percent of diaryl acid phosphate, the impurity contributed about 0.3 weight-percent of diaryl chlorophosphate to the additive. The possibility that the chlorine in the acid impurities of commercial tricresyl phosphate was involved in the effect observed by Bieber e.t at. [41] cannot be disregarded. Sanin, Shepeleva, Ulyanova and Kleimenov [42] reported that... 

Tritolyl Phosphate. Phosphoric acid iristmethyi-phenyl) ester tricresyl phosphate TCP PX-917 Celluflex Kronitex LindoL CiiH O P mol wt 368.36. C 68.47%, H 5.75%. O 17-37%. P S+4]%. A mixture of isomeric tritolyl phosphates, usually excludiug the very toxic 0rtho isomer as much as possible. Prepd from cresol and phosphoric oxychloride, phosphoric acid or pentachloride Prahl, UJ5 pat. 2,305,240 (1957) Bondy, Gumb. Brit pat. 890,642 (1962 to Coalite and Chem Prod ) Faith. Keyes Clark s Industrial Chemicals, F. A, Lowenheim M, K, Moran Eds, (Wiley-Interscience, New York, 4th ed., ]975) pp 849-853. 

Beilstein Handbook Reference) BRN 2140519 Butyl phenyl phosphate ((BuO)2(PhO)PO) CCRIS 4604 Di(n-butyl) phenyl phosphate Dibutyl phenyl phosphate EINECS 219-772-7 HSDB 2604 Phosphoric acid, dibutyl phenyl ester. 

Diethyl 0-[4-(melhylsulfinyl)phenyl] phosphoro-thioate, AI3-24945 BAY 25141 Bayer 25141 BRN 2219515 Caswell No. 343 Chemagro 25141 Daconit Dasanit Diethyl p-methylsulfinylphenyl thiophosphate p,0-Diethyl O-p-(methylsuifinyl)phenyl thiophosphate EINECS 204-114-3 ENT 24,945 EPA Pesticide Chemical Code 032701 Fensulfothion HSDB 1580 OMS 37 0,0-Diaethyl-0-4-methylsulfinyl-phenyl-monothiophos-phat 0,0-Diathyl-0-4-methylsulfinyl-phenyl-monothio-phosphat 0,0-Diethyl 0-p-(methylsulfinyl)phenyl thiophosphate 0,0-Diethyl 0-4-methylsulphinylphehyl phosphorothioate 0,0-Diethyl 0-(p-(methylsulfinyl)-phenyl) phosphorothioate 0,0-Diethyl 0-(4-(methylsulfinyl)phenyl) phosphorothioate Phenol, p-(methylsulfinyl)-, 0-ester with 0,0-diethyl phosphoro-thioate Phosphorothioic acid, 0,0-diethyl 0-(4-(methylsulfinyl)phenyl) ester S 767 Terracur P VUAgT 96 ... 

DL-a-acetamido-P-hydroxy-p-nitropropiophenone has been prepared from L-(+)-threo-(p-nitrophenyl)-2-aminopropan-l,3-diol and acetic anhydride followed by photooxidation in the presence of acidic KBrOs and HBr. Photosensitized electron transfer reactions of tri-1-naphthyl phosphate and di-1-naphthyl methyl phosphate using 9,10-dicyanoanthracene are reported to lead to the formation of 1,1 -binaphthyl, but no reaction occurs for mono-1-naphthyl and di- or tri-phenyl esters. Irradiation of bis(3,4-methylenedioxyphenyl) methylphosphonate in the presence of DCA induces single electron oxidation followed by intramolecular rearrangement and gives 2-(3,4-methylenedioxyphenyl)-3,4-methylenedioxy-phenyl methylphosponate. ... 

Synonyms phenyl phosphate phosphoric acid phenyl ester... 

Phosphoric acid, diisodecyl phenyl ester. See Diisodecyl phenyl phosphate... 

Ethyl phosphate. See Triethyl phosphate Ethylphosphonodithioic acid-O-ethyl-S-phenyl ester. SeeFonofos Ethyl phthalate. See Diethyl phthalate Ethyl phthalyl ethyl glycolate CAS 84-72-0... 

Phosphonothioic acid, methyl-, (5-ethyl-2-methyl-1,3,2-dioxaphorinan-5-yl) methyl methyl ester, p-oxide. See Methylphosphonic acid, (5-ethyl-2-methyl-2-oxido-1,3,2-dioxaphosphorinan-5-yl) methyl methyl ester Phosphonous acid, (1,1 -biphenyl)-4,4 -diylbis-, tetrakis (2,4-bis (1,1-dimethylethyl) phenyl) ester. See Tetrakis (2,4-di-t-butylphenyl)-4,4 -biphenylenediphosphonite Phosphopyridoxal. See Pyridoxal 5-phosphate Phosphoramidic acid diethyl ester. See Mephosfolan... 

Unsaturated phosphatidylinositol has been synthesized by Molotkovskii and Bergelson (1971) using an optically active glycerol derivative but a racemic myo-inositol moiety which was added from an acetylated inositol phosphate benzyl ester. Klyash-chitski et ah (1971) prepared a completely optically active dipalmitoylphosphatidylinositol. However, because they used benzyl and phenyl protecting groups their method is not suitable for unsaturated phosphatidylinositols. 

Phosphoric acid esters Ethyl metaphosphate Phosphate buffer Quinoline phosphate Dichloro phosphites, CH OPCh Triethyl phosphate. Butyl phosphate Phenyl acid phosphate Diphenyl hydrogen phosphate Di-p-nitrophenyl hydrogen phosphate (RO)gPS... 

Deoxythymidine 3 -p-aminophenylphos-phate 5 -phosphate, 358, 360 Deoxythymidine 3, 5 -diphosphate, 358 Deoxythymidine 3 -p-nitrophenylphos-phate 5 -phosphate, 358 Deoxythymidine 3 -phosphate p-nitro-phenyl ester, 358, 360 Deoxythymidine 5 -phosphate p-nitro-phenyl ester, 358... 

The nuclease requires Ca + ions for activity, with no other divalent metal ion being able to support catalysis. A large number of other phospodiester-ases have been found to be dependent on divalent metal ions for activity, including the restriction endonuclease icoRI (Barton et al, 1982). Thus elucidation of the mechanism of the reaction catalyzed by staphylococcal nuclease may provide important clues to the mechanisms of the other metal-dependent phosphodiesterases. Fortunately, staphylococcal nuclease will catalyze, albeit at a low rate, the hydrolysis of a number of mononucleotide esters (Cuatrecasas et al., 1969), including thymidine 5 -(4-nitro-phenyl phosphate) this ester is hydrolyzed to thymidine and 4-nitrophenyl phosphate. We have determined the stereochemical course of the hydrolysis of thymidine 5 -(4-nitrophenyl [ 0, 0]phosphate) and interpreted the result in terms of the structure of the active site of the enzyme. 

The SEM ester was used to protect a carboxyl group where DCC-mediated esterification caused destruction of the substrate. It was formed from the acid and SEM chloride (THF, 0°, 80% yield) and was removed solvolytically. The ease of removal in this case was attributed to anchimeric assistance by the phosphate group. Normally SEM groups are cleaved by treatment with fluoride ion. Note that in this case the SEM group is removed considerably faster than the phenyl groups from the phosphate. ... 

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