- Enzymatic synthesis of perfluoroalkylated DNA
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Thymidine analogues 5-trifluoromethyl-, 5-pentafluoroethyl- and 5-(heptafluoro-n-propyl)-2′-deoxyuridines were synthesised and converted into the corresponding 5′-triphosphates 1a-c. Performing DNA polymerase-catalyzed primer extension reactions these mod
- Holzberger, Bastian,Marx, Andreas
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Read Online
- METHOD FOR PREPARING TRIFLURIDINE
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The present application relates to a method for preparing trifluridine, comprising reacting a compound of formula III with a compound of formula IV in a first solvent in the presence of an acid to obtain a compound of formula II, and performing further reaction to obtain trifluridine.
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Paragraph 0074-0077
(2021/09/26)
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- Preparation method of perfluoroalkylated aryl compound
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The present invention provides a process for the preparation of a perfluoroalkylated aryl compound which comprises reacting an aryl compound with a perfluoroalkylsulfinate in the presence of an iron salt and hydrogen peroxide. To the method provided by the invention, perfluoroalkyl sulfinate is used as an alkylating agent, iron salt is used as a catalyst, hydrogen peroxide is used as an initiator, and the reaction time is short. The method has the characteristics of high yield, convenient operation, high safety and the like, and has wide application in the fields of drug synthesis, biological probes, fluorescent materials and the like.
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Paragraph 0120-0123
(2021/11/14)
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- Method for preparing trifluridine
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The invention discloses a method for preparing trifluridine. The method comprises the following steps of performing halogenation on ribose fully protected by hydroxyl, performing condensation on the halogenated ribose and 5-(trifluoromethyl)uracil, performing deprotection to generate an intermediate namely 5-trifluoromethyl uridine, and then performing dehydrating, halogenation and a reduction reaction so as to obtain the trifluridine. According to the method disclosed by the invention, the fully protected ribose is used as a raw material, so that the cost of raw materials can be notably reduced; besides, in the condensation reaction process of the ribose protected by 2-site acyl groups, due to effects of neighboring group participation, the beta-stereoselectivity of the condensation reaction is notably increased; the 5-(trifluoromethyl)uracil is used as a raw material, and high-toxicity trifluoromethylating reagents are avoided, so that the method is environmentally-friendly; and a compound as shown in a formula VI begins to use continuous operations, separation and purification on the intermediate are not needed, and final products can be directly generated, so that production and operation are greatly convenient, the production efficiency is improved, and the cost of human resources is reduced.
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Paragraph 0055; 0056
(2020/06/20)
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- Fluridine crystal form B and preparation method thereof
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The invention discloses a novel crystal form B of trifluridine and a preparation method thereof, wherein the novel crystal form B of trifluridine has good dissolvability and stability, and the preparation method has the advantages of simple process, high yield, high product purity, low cost and easy realization of large-scale production of the novel crystal form B of trifluridine. According to results of powder X-ray diffraction peaks, the novel crystal form B of trifluridine has characteristic peaks at the following diffraction angles 2theta (+/-0.2 DEG): 6.95 DEG, 9.66 DEG, 12.70 DEG, 14.11 DEG, 16.19 DEG, 17.58 DEG, 18.18 DEG, 19.75 DEG, 20.05 DEG, 21.57 DEG, 22.99 DEG, 23.61 DEG, 24.50 DEG, 25.80 DEG, 27.79 DEG, 28.14 DEG, 29.05 DEG, 31.06 DEG, 32.01 DEG, 33.01 DEG, 34.06 DEG, 35.62 DEG, 37.04 DEG, 38.55 DEG and 39.89 DEG. The preparation method for the novel crystal form B of trifluridine comprises the following concrete steps: adding a crude trifluridine product into purified water; carrying out heating under stirring until the crude trifluridine product is dissolved and stopping heating; carrying out cooling to room temperature under stirring; and successively carrying out crystallization, filtering and reduced pressure drying.
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Paragraph 0028-0057
(2020/06/02)
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- Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
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Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.
- Ghosh, Indrajit,Khamrai, Jagadish,Savateev, Aleksandr,Shlapakov, Nikita,Antonietti, Markus,K?nig, Burkhard
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p. 360 - 366
(2019/08/15)
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- SOLID STATE FORMS OF 5-CHLORO-6-[(2-IMINOPYRROLIDIN-1-YL)METHYL]PYRIMIDINE-2,4-(1H,3H)-DIONE HYDROCHLORIDE AND THEIR PROCESSES FOR THE PREPARATION THEREOF
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The present invention relates to solid state forms of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride compound of formula-1a and their processes for the preparation thereof and an improved process for the preparation of 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione hydrochloride. The present inventors also provides an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4-(1H,3H)-dione monohydrochloride and its process for the preparation.
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Page/Page column 41-42; 44
(2019/04/09)
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- Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated 18F-trifluoromethylation procedure
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Trifluoromethyl groups are widespread in medicinal chemistry, yet there are limited 18F-radiochemistry techniques available for the production of the complementary PET agents. Herein, we report the first radiosynthesis of the anticancer nucleoside analogue trifluridine, using a fully automated, clinically-applicable 18F-trifluoromethylation procedure. [18F]Trifluridine was obtained after two synthetic steps in 99%, and a molar activity of 0.4 GBq μmol-1 ± 0.05. Biodistribution and PET-imaging data using HCT116 tumour-bearing mice showed a 2.5 %ID g-1 tumour uptake of [18F]trifluridine at 60 minutes post-injection, with bone uptake becoming a prominent feature thereafter. In vivo metabolite analysis of selected tissues revealed the presence of the original radiolabelled nucleoside analogue, together with deglycosylated and phosphorylated [18F]trifluridine as the main metabolites. Our findings suggest a potential role for [18F]trifluridine as a PET radiotracer for elucidation of drug mechanism of action.
- King, Alice,Doepner, Andreas,Turton, David,Ciobota, Daniela M.,Da Pieve, Chiara,Wong Te Fong, Anne-Christine,Kramer-Marek, Gabriela,Chung, Yuen-Li,Smith, Graham
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p. 2986 - 2996
(2018/05/03)
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- Synthetic method of 5-trifluoromethyl uracil
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The invention discloses a synthetic method of 5-trifluoromethyl uracil prepared under simple and convenient conditions. The synthetic method is characterized in that starting from uracil and trifluoroiodomethane, after alkali is added, the 5-trifluoromethyl uracil is efficiently obtained under the irradiation of visible light. Some of products obtained are listed drug molecules or important pharmaceutical intermediates. The synthetic method has the benefits that the uracil and the trifluoroiodomethane which are cheap and easy to obtain are used as raw materials; in the reaction process, only the illumination is required, and the cheap alkali is added without the use of a catalyst; during the mass production, a solvent can be recovered through a vacuum distillation method; the synthetic method is green, economic and efficient in the whole production process and has very significant advantages compared with an existing production process.
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Paragraph 0060; 0061; 0062
(2018/09/21)
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- Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines
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Fluoroalkylated enaminones, such as trifluridine and 5-trifluoromethyluracil, have widespread applications in pharmaceuticals and agrochemicals. Although these kinds of pharmaceutical agent often bear CF3 and perfluoroalkyl motifs in the core structure, access to such analogues typically requires multi-step synthesis. Here, we report a mild, metal-free and operationally simple strategy for the direct perfluoroalkylation of uracils, cytosines and pyridinones through a visible-light induced pathway from perfluoroalkyl iodides. This photochemical transformation features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance, providing a facile route for applications in medicinal chemistry.
- Huang, Yang,Lei, Yun-Yun,Zhao, Liang,Gu, Jiwei,Yao, Qiuli,Wang, Ze,Li, Xiao-Fei,Zhang, Xingang,He, Chun-Yang
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supporting information
p. 13662 - 13665
(2019/01/03)
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- A method for preparing qu Fu uridine
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The invention discloses a preparation method of trifluridine. The method comprises the specific steps of: adding 2'-deoxyuridine and trifluoromethyl sulfinate sodium to a reaction solvent, stirring and cooling to - 5 to - 3 DEG C, introducing of nitrogen for protection, stirring to dissolve, dropwise adding tert-butyl hydroperoxide, controlling the temperature at less than 5 DEG C, heating to 60-65 DEG C for reaction, and conducting posttreatment after the reaction to obtain a finished product. The method provided by the invention has mild reaction conditions, simple operation, little side reaction, short reaction time, great reduction of feeding amount of tert-butyl hydroperoxide, great saving of the production cost, and high yield and high purity of the product, and is especially applicable to industrial production, and has significance to the quality control of medicine and clinical curative effect.
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Paragraph 0034; 0035
(2017/08/15)
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- Triplex- and duplex-forming abilities of oligonucleotides containing 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine
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A facile synthesis of 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine phosphoramidites from commercially available 2′-deoxyuridine and 2′-deoxycytidine was achieved, respectively. The obtained phosphoramidites were incorporated into oligonucleotides, and their binding affinity to double-stranded DNA (dsDNA) and single-stranded RNA (ssRNA) was evaluated by UV-melting experiments. The triplex-forming abilities of oligonucleotides including 5-trifluoromethylpyrimidine nucleobases with dsDNA were decreased. Especially, the stability of the triplex containing a trifluoromethylcytosine (CF3C)-GC base triplet was low, likely due to the low pKa of protonated CF3C by the electron-withdrawing trifluoromethyl group. A slight decrease in stability of the duplex formed with ssRNA by oligonucleotides including 5-tri-fluoromethylpyrimidine nucleobases was only observed, suggesting that they might be applicable to various ssRNA-targeted technologies using features of fluorine atoms.
- Ito, Yuta,Matsuo, Misaki,Osawa, Takashi,Hari, Yoshiyuki
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p. 982 - 988
(2018/11/10)
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- High purity qu Fu uridine preparation method (by machine translation)
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The present invention provides a high purity qu Fu uridine preparation method, as the compound 2 as the raw material, with the first under the action of the HMDS in trimethylchlorosilane reaction to obtain compound 3, compound 3 with the raw material compound 4 in catalyst b fluorinated copper under the action of the condensation, of ethanol by recrystallization to obtain compound 5, the final compound 5 in the protection under the action of the sodium methoxide, through ethanol and acetone mixed solvent (1:1) by recrystallization to obtain a high purity of the target compound 1. The method of the invention, the resulting product has high purity, the method is simple, easy to be purified, industrial and less pollution. (by machine translation)
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Paragraph 0010; 0042
(2017/05/26)
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- Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction
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We describe a simple, metal-and oxidant-free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.
- Li, Lu,Mu, Xiaoyue,Liu, Wenbo,Wang, Yichen,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 5809 - 5812
(2016/06/09)
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- THERMOSTABLE BIOCATALYST COMBINATION FOR NUCLEOSIDE SYNTHESIS
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The present invention relates to a transglycosylation method for the preparation of natural and synthetic nucleosides using a uridine phosphorylase (PyNPase, E.C. 2.4.2.3), a purine nucleoside phosphorylase (PNPase, E.C. 2.4.2.1), or a combination thereof. These biocatalysts may be used as such, or by means of host cells transformed with vectors comprising recombinant DNA gene derived from hyperthermophilic archaea and encoding for the PyNPase and PNPase enzymes.
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Paragraph 0088-0089
(2016/08/17)
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- Nucleoside 2′-deoxyribosyltransferase from psychrophilic bacterium Bacillus psychrosaccharolyticus - Preparation of an immobilized biocatalyst for the enzymatic synthesis of therapeutic nucleosides
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Nucleoside 2′-deoxyribosyltransferase (NDT) from the psychrophilic bacterium Bacillus psychrosaccharolyticus CECT 4074 has been cloned and produced for the first time. A preliminary characterization of the recombinant protein indicates that the enzyme is an NDT type II since it catalyzes the transfer of 2′-deoxyribose between purines and pyrimidines. The enzyme (BpNDT) displays a high activity and stability in a broad range of pH and temperature. In addition, different approaches for the immobilization of BpNDT onto several supports have been studied in order to prepare a suitable biocatalyst for the one-step industrial enzymatic synthesis of different therapeutic nucleosides. Best results were obtained by adsorbing the enzyme on PEI-functionalized agarose and subsequent cross-linking with aldehyde-dextran (20 kDa and 70% oxidation degree). The immobilized enzyme could be recycled for at least 30 consecutive cycles in the synthesis of 2′-deoxyadenosine from 2′-deoxyuridine and adenine at 37 °C and pH 8.0, with a 25% loss of activity. High conversion yield of trifluridine (64.4%) was achieved in 2 h when 20 mM of 2′-deoxyuridine and 10 mM 5-trifluorothymine were employed in the transglycosylation reaction catalyzed by immobilized BpNDT at 37 °C and pH 7.5.
- Fresco-Taboada, Alba,Serra, Immacolata,Fernandez-Lucas, Jesus,Acebal, Carmen,Arroyo, Miguel,Terreni, Marco,De La Mata, Isabel
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p. 11231 - 11249
(2014/11/08)
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- Catalytic C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds
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A copper(I)-catalyzed, regioselective C-H α-trifluoromethylation of α,β-unsaturated carbonyl compounds using Togni's reagent was developed. Diverse substrates, including enones as well as α,β- unsaturated esters, thioesters, and amides, stereospecifically afforded the corresponding (E)-α-trifluoromethylated products in moderate to high yields. Further, this method was applied to the C-H trifluoromethylation of drugs.
- Fang, Zhongxue,Ning, Yongquan,Mi, Pengbing,Liao, Peiqiu,Bi, Xihe
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supporting information
p. 1522 - 1525
(2014/04/03)
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- A comparison between immobilized pyrimidine nucleoside phosphorylase from Bacillus subtilis and thymidine phosphorylase from Escherichia coli in the synthesis of 5-substituted pyrimidine 2′-deoxyribonucleosides
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Pyrimidine nucleoside phosphorylase from Bacillus subtilis (BsPyNP, E.C. 2.4.2.3) and thymidine phosphorylase from Escherichia coli (EcTP, E.C. 2.4.2.4) were used, as immobilized enzymes, in the synthesis of 5-halogenated pyrimidine 2′-deoxyribonucleosides (14-18) by transglycosylation in fully aqueous medium. From the comparative study of the two biocatalysts, no remarkable differences emerged about their substrate specificity, bioconversion yield, stability in organic cosolvents (DMF and MeCN). Moreover, both biocatalysts could be recycled for at least 5 times with no loss of the productivity. Both enzymes do not accept arabinonucleosides and 2′,3′- dideoxynucleosides as substrates, whereas they catalyze bioconversions involving 5′-deoxyribonucleosides and 5-halogenated uracils. The synthesis of compounds 14-18 proceeded at a similar conversion (33-68% for BsPyNP and 25-62% for EcTP, respectively). Immobilization was found to exert, for both the biocatalysts, a dramatic enhancement of stability upon incubation in MeCN. Optimization of 5-fluoro-2′-deoxyuridine (14) synthesis (pH 7.5, 10 mM phosphate buffer, nucleoside/nucleobase 3:1 molar ratio) and subsequent scale-up afforded the target compound in 73% (EcTP) or 76% (BsPyNP) conversion (about 9 g/L).
- Serra, Immacolata,Bavaro, Teodora,Cecchini, Davide A.,Daly, Simona,Albertini, Alessandra M.,Terreni, Marco,Ubiali, Daniela
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- One-pot approach to functional nucleosides possessing a fluorescent group using nucleobase-exchange reaction by thymidine phosphorylase
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Herein, we describe β-selective coupling between a modified uracil and a deoxyribose to produce functionalized nucleosides catalyzed by thymidine phosphorylase derived from Escherichia coli. This enzyme mediates nucleobase-exchange reactions to convert unnatural nucleosides possessing a large functional group such as a fluorescent molecule, coumarin or pyrene, linked via an alkyl chain at the C5 position of uracil. 5-(Coumarin-7-oxyhex-5- yn)uracil (C4U) displayed 57.2% conversion at 40% DMSO concentration in 1.0 mM phosphate buffer pH 6.8 to transfer thymidine to an unnatural nucleoside with C4U as the base. In the case of using 5-(pyren-1-methyloxyhex-5-yn)uracil (P4U) as the substrate, TP also could catalyse the reaction to generate a product with a very large functional group at 50% DMSO concentration (21.6% conversion). We carried out docking simulations using MF myPrest for the modified uracil bound to the active site of TP. The uracil moiety of the substrate binds to the active site of TP, with the fluorescent moiety linked to the C5 position of the nucleobase located outside the surface of the enzyme. As a consequence, the bulky fluorescent moiety binding to uracil has little influence on the coupling reaction.
- Hatano, Akihiko,Kurosu, Masayuki,Yonaha, Susumu,Okada, Munehiro,Uehara, Sanae
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p. 6900 - 6905
(2013/10/08)
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- Synthesis of nucleoside-based antiviral drugs in ionic liquids
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Nucleoside-based antiviral drugs have been synthesized using imidazolium-based ionic liquids as reaction medium. The ionic liquids were proved to be better solvents for all the nucleoside in terms of solubility and reaction medium as compared to conventional molecular solvents.
- Kumar, Vineet,Malhotra, Sanjay V.
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supporting information; experimental part
p. 5640 - 5642
(2009/06/18)
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- NUCLEIC ACID BASE HAVING PERFLUOROALKYL GROUP AND METHOD FOR PRODUCING THE SAME
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Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.
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Page/Page column 43-44
(2008/12/07)
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- Modified oligonucleotides and applications thereof
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Disclosed, among other things, are primers containing certain modified nucleobases in the 3′ terminal region of the primers that provide reduced formation of primer-dimers during amplification reactions, and various methods of use thereof.
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- Importance of 3′-hydroxyl group of the nucleosides for the reactivity of thymidine phosphorylase from Escherichia coli
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Thymidine phosphorylase in phosphate buffer catalyzed the conversion of thymidine to unnatural nucleosides. The 3′-OH, but not the 5′-OH of ribosyl moiety is necessary to be recognized as a substrate. Thus 3′-deoxythymidine could not convert to 5-fluorouracil-2′,3′- dideoxyribose. However, 5′-deoxythymidine was converted to 5-fluorouracil-2′,5′-dideoxyribose. Copyright
- Hatano, Akihiko,Harano, Aiko,Kirihara, Masayuki
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p. 232 - 233
(2007/10/03)
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- Synthesis of trifluorothymidine: Green glycosylation condition using neither chloroform nor transition metals
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A new green glycosylation condition useful for efficient large-scale preparation of trifluorothymidine 1 is described. The condition requires neither CHCl3 nor transition-metal catalysts for β-selectivity at the anomeric C1-position, which is advantageous for process development of active pharmaceutical ingredients such as 1. Key features of the condition include: (1) only an equimolar amount of trifluorothymine 2 is required, (2) the glycosylation is performed under high concentration, (3) the reaction is carried out at 50 °C to enhance the reaction.
- Komatsu, Hironori,Umetani, Hideki
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p. 847 - 850
(2013/09/06)
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- Process for the production of asymmetrical phosphoric acid diesters
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The present invention concerns a process for the production of asymmetrical phosphoric acid diesters. The process is characterized in that a phosphoric acid ester is condensed with a compound containing hydroxy groups in the presence of an arylsulfonic acid chloride and an organic base, the residue of evaporation is stirred out with an organic solvent after the hydrolysis, the arylsulfonic acid pyridine salt which forms is nearly completely crystallized and recycled, the lipid derivative that is formed is precipitated as a sparingly soluble salt by addition of a solution containing alkaline-earth ions and isolated, the sparingly soluble salt is isolated as the free acid in an organic solvent by suspension in a water-immiscible organic solvent and a dilute aqueous mineral acid, the crude product is purified if desired, by means of preparative chromatography on a RP phase and subsequently the free acid is converted if desired into any desired salt.
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- Antiviral agents
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Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.
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- THE SYNTHESIS OF 2'-DEOXY-5-TRIFLUOROMETHYLURIDINE UTILIZING A COUPLING REACTION
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The coupling reaction between 1-α-chloro-2-deoxyribose derivative and silylated 5-trifluoromethyluracil was examined.The best stereoselectivity was obtained when the reaction was carried out using a large amount of silylated base in the presence of anhydrous zinc chloride.
- Kawakami, Hiroshi,Ebata, Takashi,Koseki, Koshi,Matsushita, Hajime,Naoi, Yoshitake,et al.
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p. 569 - 574
(2007/10/02)
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- REGIOSELECTIVE DEPROTECTION OF 3',5'-O-ACYLATED PYRIMIDINE NUCLEOSIDES BY LIPASE AND ESTERASE
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A lipase was found to catalyze the regioselective hydrolysis at the secondary hydroxyl group of 2'-deoxy 3',5'-di O-hexanoyl pyrimidine nuclosides, whereas a protease catalyzes that at the primary hydroxyl group.
- Uemura, Atsuhiko,Nozaki, Kenji,Yamashita, Jun-ichi,Yasumoto, Mitsugi
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p. 3819 - 3820
(2007/10/02)
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- Studies on Organic Fluorine Compounds. Part 35. Trifluoromethylation of Pyrimidine- and Purine-nucleosides with Trifluoromethyl-Copper Complex
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Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl-copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder.The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine, -deoxycytidine, and arabinosylcytosine; 8-trifluoromethyl-adenosine, -deoxyadenosine, and -inosine; and 6-trifluoromethylribofuranosylpurine.This procedure offers simple synthesis of many trifluoromethyl compounds.
- Kobayashi, Yoshiro,Yamamoto, Kenjiro,Asai, Toyohira,Nakano, Masanori,Kumadaki, Itsumaro
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p. 2755 - 2761
(2007/10/02)
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