- Utilization of 1,3-Dioxolanes in the Synthesis of α-branched Alkyl and Aryl 9-[2-(Phosphonomethoxy)Ethyl]Purines and Study of the Influence of α-branched Substitution for Potential Biological Activity
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Syntheses of α-branched alkyl and aryl substituted 9-[2-(phosphonomethoxy)ethyl]purines from substituted 1,3-dioxolanes have been developed. Key synthetic precursors, α-substituted dialkyl [(2-hydroxyethoxy)methyl]phosphonates were prepared via Lewis acid mediated cleavage of 1,3-dioxolanes followed by reaction with dialkyl or trialkyl phosphites. The best preparative yields were achieved under conditions utilizing tin tetrachloride as Lewis acid and triisopropyl phosphite. Attachment of purine bases to dialkyl [(2-hydroxyethoxy)methyl]phosphonates was performed by Mitsunobu reaction. Final α-branched 9-[2-(phosphonomethoxy)ethyl]purines were tested for antiviral, cytostatic and antiparasitic activity, the latter one determined as inhibitory activity towards Plasmodium falciparum enzyme hypoxanthine-guanine-xanthine phosphoribosyltransfesase. In most cases biological activity was only marginal.
- Pomeisl, Karel,Pohl, Radek,Snoeck, Robert,Andrei, Graciela,Kre?merová, Marcela
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p. 119 - 156
(2019/01/04)
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- Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof
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The invention belongs to the field of medicine chemistry and particularly relates to a cholic acid-alpha-amino phosphonate derivative and a preparation method thereof.Cholic acid and phosphate ester serve as raw materials, and the cholic acid-alpha-amino
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Paragraph 0015; 0016; 0026; 0030
(2016/10/09)
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- Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof
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The invention belongs to the field of pharmaceutical chemistry and particularly relates to novel bile acid-alpha-hydroxyphosphonate compounds and a preparation method thereof. Bile acid and phosphate ester are taken as raw materials, the bile acid-alpha-h
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Paragraph 0017; 0018; 0020; 0021
(2016/12/22)
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- A kind of rare earth metal arylamine compound and its preparation method and application
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The invention discloses a rare-earth metal arylamine group compound as well as preparation method and application thereof. The invention discloses the rare-earth metal arylamine group compound which is characterized in that a general formula of the rare-e
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Paragraph 0071-0072
(2017/01/17)
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- N -BuLi as a highly efficient precatalyst for hydrophosphonylation of aldehydes and unactivated ketones
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It was found for the first time that organic alkali metal compounds serve as highly efficient precatalysts for the hydrophosphonylation reactions of aldehydes and unactivated ketones with dialkyl phosphite under mild conditions. For ketone substrates, a reversible reaction was observed, and the influence of catalyst loading and reaction temperature on the reaction equilibrium was studied in detail. Overall, the hydrophosphonylation reactions catalyzed by 0.1 mol % n-BuLi were completed within 5 min for a broad range of substrates and generated a series of α-hydroxy phosphonates in high yields.
- Liu, Chengwei,Zhang, Yu,Qian, Qinqin,Yuan, Dan,Yao, Yingming
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supporting information
p. 6172 - 6175
(2015/01/09)
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- Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates
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(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.
- Xu, Liang,You, Geyun,Peng, Hao,He, Hongwu
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p. 812 - 818
(2014/07/08)
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- Copper-catalyzed synthesis of α-hydroxy phosphonates from H-phosphonates and alcohols or ethers
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Easy PC: α-Hydroxy phosphonates were synthesized by copper/tert-butyl hydroperoxide (TBHP)-catalyzed oxidative addition reactions of H-phosphonates with alcohols or ethers. Diverse α-hydroxy phosphonates were obtained from substituted benzyl alcohols or alkyl alcohols and alkyl ethers in moderate to good yields. Copyright
- Zhao, Zengxiang,Xue, Wanhua,Gao, Yuxing,Tang, Guo,Zhao, Yufen
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supporting information
p. 713 - 716
(2013/05/09)
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- Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
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An extremely simple, high yielding, highly rapid and solvent-free protocol has been described for hydrophosphylation of aldehydes using potassium phosphate as catalyst. Easy commercial availability of the reusable catalyst, operational simplicity at ambie
- Kulkarni, Makarand A.,Lad, Uday P.,Desai, Uday V.,Mitragotri, Satish D.,Wadgaonkar, Prakash P.
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p. 148 - 152
(2013/04/24)
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- Lanthanide amides [(Me3Si)2N]3Ln(μ-Cl) Li(THF)3 catalyzed hydrophosphonylation of aryl aldehydes
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A highly efficient method for the synthesis of α-hydroxy phosphonates via lanthanide amides [(Me3Si)2N]3Ln(μ-Cl) Li(THF)3 catalyzed hydrophosphonylation of aromatic aldehydes was developed. The reactions produce
- Wu, Qingmao,Zhou, Jun,Yao, Zhigang,Xu, Fan,Shen, Qi
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supporting information; experimental part
p. 7498 - 7501
(2011/02/21)
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- Synthesis, characterizations, and crystal structures of α-hydroxyphosphonic acid esters
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This article describes the synthesis of -hydroxyphosphonic acid esters using the Pudovik reaction. IR, 1H NMR, 13C NMR, 31P NMR, MS, and elemental analysis were employed to confirm their structures. X-ray structure analysi
- Fang, Hua,Chen, Weizhu,Hong, Bihong,Zhao, Yufen,Fang, Meijuan
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experimental part
p. 2182 - 2193
(2010/12/25)
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- Asymmetric hydrogenation of α-keto phosphonates with chiral palladium catalysts
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Under atmospheric hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and (R)-MeO-BIPHEP in 2,2,2-trifluoroethanol promoted the asymmetric hydrogenation of diisopropyl α-keto phosphonates 1 to afford the corresponding α-hydroxy phospho
- Goulioukina, Nataliya S.,Bondarenko, Grigorii N.,Bogdanov, Alexei V.,Gavrilov, Konstantin N.,Beletskaya, Irina P.
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experimental part
p. 510 - 515
(2009/07/19)
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- Straightforward synthesis of a new series of α-(arylamino thiocarbonyloxy) hydrocarbylphosphonates
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A convenient, straightforward, two-step reaction of α- hydroxyhydrocarbylphosphonates with arylisothiocyanates in the presence of catalytic amounts of sodium methoxide in 1,2-dichloroethane as solvent produced various new α-(arylamino thiocarbonyloxy) hyd
- Li, Jian-Ping,Zhu, Jun-Ge,Liu, Rui-Jie,Cui, Feng-Ling,Liu, Ping,Liu, Guo-Sheng
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- The preparation of dialkyl 1-hydroxyalkylphosphonates in the reaction of trialkyl phosphites with oxonium salts derived from aldehydes or ketones
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The reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates via Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is a very convenient instant method for the preparation of dialkyl 1-hydroxyalkylphosphonates with a good yield as an alternative to the well-known Abramov reaction. Georg Thieme Verlag Stuttgart.
- Goldeman, Waldemar,Soroka, Miroslaw
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p. 3019 - 3024
(2008/02/08)
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- Enzymes in Organic Chemistry, Part 1: Enantioselective Hydrolysis of α-(Acyloxy)phosphonates by Esterolytic Enzymes
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α-Hydroxyphosphonates (+/-)-3 were prepared and transformed into esters (+/-)-5.Eight lipases as well as pig liver esterase were tested as catalysts for enantioselective hydrolyses of α-(acyloxy)phosphonates in a biphasic system.Two of them proved to be useful.The highest enantioselectivity was obtained with lipase F-AP 15 and α-(acetyloxy)phenylmethylphosphonates (+/-)-5a and (+/-)-5b as substrates.The (S)-enantiomers were exclusively hydrolyzed to give optically pure alcohols (S)-(-)-3a and (S)-(-)-3b.Lipases AP 6 and F-AP 15 were used to prepare phosphonates(S)-(-)-3b, (S)-(+)-3d and (S)-(-)-3e on a preparative scale with an enantiomeric excess of 81percent, 87percent, and 89percent, respectively.The absolute configurations of the α-hydroxyphosphonates were assigned by Horeau's method and 1H NMR spectroscopy of Mosher's derivatives.
- Li, Yong-Fu,Hammerschmidt, Friedrich
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p. 109 - 120
(2007/10/02)
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