- Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose
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The invention relates to the field of organic synthesis, in particular to a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose, which comprises the following steps: mixing D-ribose with methanol and a catalyst, heating to react, neutralizing, and concentrating to obtain a methyl esterification intermediate III; mixing the methyl esterification intermediate III with an organic solvent, 4-dimethylaminopyridine and an acid-binding agent, cooling, dropwise adding benzoyl chloride for reaction, washing with water for layering, and drying to obtain a benzoylated intermediateII; finally, mixing the benzoylated intermediate II with an organic solvent and acetic anhydride, then adding a catalyst, stirring, carrying out heat preservation reaction for 10-20 hours at the temperature of 0-70 DEG C, and after the reaction is qualified, cooling, crystallizing and centrifuging to obtain a crude product; finally, performing recrystallization and centrifugal drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose, and obtaining the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose. The method has the advantages of short reaction steps, high chemicaland optical purity, simple operation, easily available raw materials, low cost, small amount of three wastes, environmental friendliness and the like, and is suitable for industrial production.
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- 2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations
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The global public health concerns and economic impact caused by emerging outbreaks of RNA viruses call for the search for new direct acting antiviral agents. Herein, we describe the synthesis, DFT calculations, and antiviral evaluation of a series of novel 2-hydroxyimino-6-aza-pyrimidine ribonucleosides. DFT//B3LYP/6-311+G?? calculations of the tautomeric distributions of the 2-hydroxyimino nucleosides 7, 8, and 9 in aqueous environments indicate a predominance of the canonical 2-(E)-hydroxyimino structure, where the hydroxyl group points away from the sugar moiety. The conformer distributions of the latter geometrical isomers of 7, 8, and 9 support the formation of five membered rings via hydrogen bonding between the (E)-C2N-O-H moiety and N3-H of 7 and 8 and between (E)-C2N-O-H and N3 of 9, creating purine shaped nucleosides with the glycosidic linkage at the pyrimidine ring. The newly synthesized nucleosides were screened against an RNA viral panel, of which moderate antiviral activity was observed against Zika virus (ZIKV) and human respiratory syncytial virus (HRSV). 6-Aza-2-hydroxyimino-5-methyluridine derivative 18 showed activity against ZIKV (EC50 3.2 μM), while its peracetylated derivative 19 showed activity against HRSV (EC50 5.2 μM). The corresponding 4-thiono-2-hydroxyimino derivative 8 showed activity against HRSV (EC50 6.1 μM) and against ZIKA (EC50 2.4 μM). This study shows that the 6-aza-2-hydroxyimino-5-methyluracil derived nucleosides can be further optimized to provide potent antiviral agents. This journal is
- Abou-Elkhair, Reham A. I.,Wasfy, Abdalla A.,Mao, Song,Du, Jinxi,Eladl, Sobhy,Metwally, Kamel,Hassan, Abdalla E. A.,Sheng, Jia
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p. 19650 - 19662
(2020/12/05)
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- 3-Trifluoromethylpyrazolones derived nucleosides: Synthesis and antiviral evaluation
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Dengue (DENV) viral infection is a global public health problem that infrequently develops life threatening diseases such as dengue hemorrhagic fever (DFS) and dengue shock syndrome (DSS). Middle East respiratory syndrome coronavirus (MERS-CoV) is a highly pathogenic human corona virus with 38% fatality rate of infected patients. A series of 4-arylhydrazono-5-trifluoromethyl-pyrazolones, their ribofuranosyl, and 5′-deoxyribofuranosyl nucleosides were synthesized, geometry optimized using Density functional theory (DFT), and evaluated for their antiviral activity. 2-Nitrophenylhydrazonopyra-zolone derivative 5 showed significant activity against MERS-CoV (EC50 = 4.6 μM). The nucleoside analog 8 showed moderate activity against DENV-2 (EC50 = 10 μM), while the activity was abolished with the corresponding 5′-deoxyribonucleoside analogs. The identified hits in this study set this category of compounds for further future optimizations.
- Ahmed, Ayman M. S.,Abou-Elkhair, Reham A. I.,El-Torky, Alaa M.,Hassan, Abdalla E. A.
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p. 590 - 603
(2019/04/03)
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- COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE
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Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.
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Paragraph 0069
(2019/04/09)
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- A process for preparing 1 - O - acetyl - 2, 3, 5 - three - O - benzoyl - β - D - ribofuranosyl method (by machine translation)
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A process for preparing 1 - O - acetyl - 2, 3, 5 - three - O - benzoyl - β - D - ribofuranosyl method, including: S1, benzoylated reaction: the adenosine with organic solvent and mixed acid, dropping benzoyl chloride reaction, filtering, the filter cake washed with organic solvent, the filtrate, concentrating and recovering organic solvent to dry, adding methanol stirring beating, filtering, to obtain the [...]; S2, acylation reaction: [...] with the cosolvent and acetic anhydride mixing, stirring solution cleaning, dropping of a catalytic amount of paratoluenesulfonic acid, thermal insulation reaction, filtering, spend solvent washing the filter cake, the filtrate, washing filtrate, dried anhydrous magnesium sulfate, filtered, concentrated under reduced pressure for recovering the solvent, to obtain crude, recrystallization, get. The invention not only avoids the use of pyridine malodorous materials, but also has the step is short, the operation is simple, low cost, environment-friendly, "three wastes" less amount and the like, suitable for industrial production. (by machine translation)
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Paragraph 0012; 0013; 0016; 0018; 0020
(2018/10/11)
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- Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer
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A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.
- Thiesen, Luciano J. Hoeltgebaum,Cabral, Nadia,Joselice E Silva, Maria,Bezerra, Gilson,Doboszewski, Bogdan
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p. 249 - 264
(2017/06/19)
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- L-nucleoside compounds and application thereof
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The invention discloses L-nucleoside compounds having the structure characteristic represented by the formula (I) or pharmaceutically acceptable salts thereof, and belongs to the technical field of pharmaceutical chemistry. The compounds can inhibit the activity of RNA viral polymerase, so the compounds can be used as potential drugs for prevention and treatment of infection of RNA viruses such as HCV, influenza virus, HRV (rhinovirus), RSV, Ebola virus, dengue virus, intestinal virus and the like.
- -
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Paragraph 0138; 0142
(2016/11/02)
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- Synthesis of 6-(het) ary Xylocydine analogues and evaluating their inhibitory activities of CDK1 and CDK2 in vitro
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A series of purine nucleoside analogues bearing an aryl and hetaryl group in position 6 were prepared and their biological activities were assessed by in vitro CDK1/Cyclin B1 and CDK2/Cyclin A2 kinase assay. From the synthesized chemicals, three Xylocydine derivatives 3h, 3i, and 3j exhibited specific inhibitory activities on CDK2/Cyclin A2 with IC50 values of 4.6, 4.8, and 55 μM, respectively. Those three compounds all induced G1/S phase arrest in Human epithelial carcinoma cell line (HeLa), and the results suggested they may inhibit CDK2 activity in vitro. Furthermore, molecular modeling study, their docking into Cyclin Dependant Kinase 2 (CDK2) active site showed high docking scores. Taken together, these data suggest that, those three compounds are good inhibitors of CDK2 for studying this kinase signal transduction pathway in cell system.
- Xiao, Chuan,Sun, Chao,Han, Weiwei,Pan, Feng,Dan, Zhu,Li, Yu,Song, Zhi-Guang,Jin, Ying-Hua
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p. 7100 - 7110
(2012/01/14)
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- 2'-FLUORO-4'-SUBSTITUTED NUCLEOSIDES, THE PREPARATION AND USE
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The present invention provides 2'-fluorine-4'-substituted-nucleoside analogues or their pro-drugs or 5'-phosphate esters (including the pro-drugs of the 5'-phosphate esters), preparation methods and uses thereof. The compounds have the general formula as follows: wherein: R = CH3, CH, N3, C≡CH; R' = H, F; X = F, OH, NH2; Y = H, CH3, F, OH, NH2 The compounds are used in the synthesis of drugs for the treatment of virus infection, especially for the treatment of HBV, HCV or HIV infection.
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Page/Page column 11
(2010/05/13)
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- Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides
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The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-Lribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac + as the catalytically active species was clarified, proving that the anomerization of the acylated methyl furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated methyl furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage.
- Forsman, Jonas J.,Waerna, Johan,Murzin, Dmitry Yu,Leino, Reko
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experimental part
p. 5666 - 5676
(2010/03/03)
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- METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE
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An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.
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Page/Page column 13
(2009/10/06)
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- Reaction kinetics and mechanism of acid-catalyzed anomerization of 1-O-acetyl-2,3,5-tri-O-benzoyl-l-ribofuranose
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The mechanism of the acid-catalyzed anomerization of 1-O-acetyl-2,3,5-O-benzoyl-α- and -β-l-ribofuranoses in different acetic acid-acetic anhydride mixtures was investigated. The progress of the reactions was followed by NMR spectroscopy and the rate cons
- Forsman, Jonas J.,Waerna, Johan,Murzin, Dmitry Yu.,Leino, Reko
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body text
p. 1102 - 1109
(2009/09/05)
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- Synthesis of 2-(5-azido-5-deoxy-β-D-ribofuranosyl)-4-methyl-5-nitro-1, 2,3-triazole
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The synthesis of 2-(5-azido-5-deoxy-β-D-ribofuranosyl)-4-methyl-5- nitro-1,2,3-triazole has been accomplished in 5 steps starting from D-ribose.
- Banda, Geetha,Srinivasulu,Ugandhar,Chakravarthy
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p. 1920 - 1923
(2007/10/03)
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- A solid-phase approach to novel purine and nucleoside analogs
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This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbrueggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective oxidation-reduction procedure of the 2-OH group. Some compounds exhibited moderate activity against HIV-1 in PBM cells.
- Chang, Junbiao,Dong, Chunhong,Guo, Xiaohe,Hu, Weidong,Cheng, Senxiang,Wang, Qiang,Chen, Rongfeng
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p. 4760 - 4766
(2007/10/03)
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- 2'-deoxy-L-nucleosides
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This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH2, NHR′, or NR′R″Z is H, F, Cl, Br, I, CN, or NH2. R is hydrogen, halogen, lower alkyl of C1-C6 or aralkyl, NO2, NH2, NHR′, NR′R″, OH, OR, SH, SR, CN, CONH2, CSNH2, CO2H, CO2R′, CH2CO2H, CH2CO2R′, CH═CHR, CH2CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C1-C6. R13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and
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Page/Page column 35
(2010/02/11)
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- Synthesis and biological evaluation of novel apio nucleosides with thiazole-4-carboxamide and 1,2,4-triazole-3-carboxamide
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In view of biological activities of azole nucleosides and apio-dideoxynucleoside, novel apio nucleoside analogues (1 and 2) with thiazole and triazole base moiety were synthesized using 2,3-O-isopropylidene-apio-β -D-furanose (3), which was prepared from D-mannose.
- Kim, Myong Jung,Jeong, Lak Shin,Kim, Joong Hyup,Shin, Ji Hye,Chung, Soon Yong,Lee, Sang Kook,Chun, Moon Woo
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p. 715 - 724
(2007/10/03)
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- Monocyclic L-nucleosides, analogs and uses thereof
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Novel monocyclic L- nucleoside compounds have general formula (I). Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th 1 and Th 2 response.
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- Methods of treating hepatitis delta virus infection with beta-l-2'-deoxy-nucleosides
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A method and composition for treating a host infected with hepatitis D comprising administering an effective hepatitis D treatment amount of a described 2′-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof.
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- PROCESS FOR THE PREPARATION OF 2'- FLUORO-5-METHYL-BETA-L-ARABINO- FURANOSYLURIDINE
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The present invention relates to a novel and improved process for preparing 2′-fluoro-5-methyl-β-L-arabinofuranosyluridine represented by formula (1) which shows anti-viral activity, especially potent anti-viral activity against hepatitis B-virus and Epstein-Barr virus:
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- β-L-2'-deoxy-nucleosides for the treatment of hepatitis B
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This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2''-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2''-deoxy-β-L-erythro-pentofuranonucleoside has the formula: STR1wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2''-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2''-deoxy-β-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.
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- β-L-2'-deoxy-nucleosides for the treatment of hepatitis B
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This invention is directed to a method for treating a host infected with hepatitis B comprising administering an effective amount of an anti-HBV biologically active 2′-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof, wherein the 2′-deoxy-β-L-erythro-pentofuranonucleoside has the formula: wherein R is selected from the group consisting of H, straight chained, branched or cyclic alkyl, CO-alkyl, CO-aryl, CO-alkoxyalkyl, CO-aryloxyalkyl, CO-substituted aryl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, amino acid residue, mono, di, or triphosphate, or a phosphate derivative; and BASE is a purine or pyrimidine base which may be optionally substituted. The 2′-deoxy-β-L-erythro-pentofuranonucleoside or a pharmaceutically acceptable salt or prodrug thereof may be administered either alone or in combination with another 2′-deoxy-β-L-erythro-pentofuranonucleoside or in combination with another anti-hepatitis B agent.
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- Monocyclic L-Nucleosides, analogs and uses thereof
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Novel monocyclic L-Nucleoside compounds have the general formula STR1 Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.
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- L-ribonucileosides for racemic RNA
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Two L-ribosyl donors were synthesised from L-xylose, then submitted to a glycosidation reaction according to Vorbruggen's conditions to furnish L- ribonucleosides in high yield.
- Moyroud,Botta,Strazewski
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p. 693 - 695
(2007/10/03)
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- A practical synthesis of L-FMAU from L-arabinose
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A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.
- Du, Jinfa,Choi, Yongseok,Lee, Kyeong,Chun, Byoung K.,Hong, Joon H.,Chu, Chung K.
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p. 187 - 195
(2007/10/03)
-
- Synthesis and testing of new modified nucleosides
-
New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-c and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analogues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.
- Jung, Michael E.,Nichols, Christopher J.,Kretschik, Oliver,Xu, Yue
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p. 541 - 546
(2007/10/03)
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- L-Ribonucleosides from L-xylose
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L-Xylose was converted into a L-ribose derivative via an oxidation/reduction procedure. The L-ribosyl donor was submitted to a glycosidation reaction according to Vorbruggen's conditions to give L- ribonucleosides (L-uridine, L-cytidine, L-adenosine and L-guanosine) in high yield.
- Moyroud, Elisabeth,Strazewski, Peter
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p. 1277 - 1284
(2007/10/03)
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- Efficient syntheses of L-ribose and 2-deoxy L-ribose from D-ribose and L-arabinose
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Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14.
- Jung, Michael E.,Xu, Yue
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p. 4199 - 4202
(2007/10/03)
-
- Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-L-arabino- furanosyl)pyrimidine nucleosides as anti-hepatitis B virus agents
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Since 2'-fluoro-5-methyl-β-L-arabinofuranosyluracil (L-FMAU) has been shown to be a potent anti-HBV agent in vitro, it was of interest to study the structure-activity relationships of related nucleosides. Thus, a series of 1- (2-deoxy-2-fluoro-β-L-arabinofuranosyl)pyrimidine nucleosides have been synthesized and evaluated for antiviral activity against HBV in 2.2.15 cells. For this study, L-ribose was initially used as the starting material. Due to the commercial cost of L-ribose, we have developed an efficient procedure for the preparation of L-ribose derivative 6. Starting from L-xylose, 6 was obtained in an excellent total yield (70%) through the pyridinium dichromate oxidation of the 3-OH group followed by stereoselective reduction with NaBH4. It was further converted to the 1,3,5-tri-O-benzoyl-2-deoxy-2- fluoro-α-L-arabinofuranose (10), which was then condensed with various 5- substituted pyrimidine bases to give the nucleosides. Among the compounds synthesized, the lead compound, L-FMAU (13), exhibited the most potent anti- HBV activity (EC50 0.1 μM). None of the other uracil derivatives showed significant anti-HBV activity up to 10 μM. Among the cytosine analogues, the cytosine (27) and 5-iodocytosine (35) derivatives showed moderately potent anti-HBV activity (EC50 1.4 and 5 μM, respectively). The cytotoxicity of these nucleoside analogues has also been assessed in 2.2.15 cells as well as CEM cells. None of these compounds displayed any toxicity up to 200 μM in 2.2.15 cells. Thus, compound 13 (L-FMAU), 27, and 35 showed a selectivity of over 2000, 140, and 40, respectively.
- Ma, Tianwei,Pai, S. Balakrishna,Zhu, Yong Lian,Lin, Ju Sheng,Shanmuganathan, Kirupa,Du, Jinfa,Wang, Chunguang,Kim, Hongbum,Newton, M. Gary,Cheng, Yung Chi,Chu, Chung K.
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p. 2835 - 2843
(2007/10/03)
-
- ON THE CONVERSION OF ARABINO- AND RIBOFURANOSYL METHYL GLYCOSIDES TO THEIR 1-O-ACETYL DERIVATIVES
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Improved conditions for the acetolysis of methyl 2,3,5-tri-O-benzyl-α- and β-L-arabinofuranosides and 2,3,5-tri-O-benzoyl-α- and β-L-ribofuranosides have been investigated.In the case of the arabinofuranosides, reproducible acetolysis conditions were obtained by substantially decreasing the amount of sulphuric acid with respect to acetic acid-acetic anhydride mixtures.With the ribofuranosides low temperature acetolysis for a short time resulted in good isolated yield of the β-1-O-acetyl anomer.
- Cimpoia, Alex R.,Hunter, Patricia J.,Evans, Colleen A.,Jin, Haolun,Breining, Tibor,Mansour, Tarek S.
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p. 1115 - 1120
(2007/10/02)
-
- SYNTHESIS OF 5-HYDROXY-6-METHYLURACIL 3β-D-RIBOFURANOSIDE
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3-(β-D-Ribofuranosyl)-5-hydroxy-6-methyluracil was synthesized by the silyl method in the presence of SnCl4 using 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose as the carbohydrate component.The structures of the glycosides were confirmed by spectral methods.
- Tolstikov, G. A.,Baltina, L. A.,Khalilov, L. M.,Spirikhin, L. V.,Sultanmuratova, V. R.,Murinov, Yu. I.
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p. 623 - 626
(2007/10/02)
-
- Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
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2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.
- Baud,Chavis,Lucas,Imbach
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p. 4437 - 4440
(2007/10/02)
-
- Antiviral Nucleosides. A Stereospecific, Total Synthesis of 2'-Fluoro-2'-deoxy-β-D-arabinofuranosyl Nucleosides
-
A general, total synthesis of (2'-fluoro-2'-deoxy-β-D-arabinofuranosyl)uracils 1a-d is described.A study of the coupling reaction beetwen 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (7) and silylated pyrimidines 11a-d has resulted in a high overall yield for the five-step stereospecific synthesis of β-nucleosides.
- Howell, Henry G.,Brodfuehrer, Paul R.,Brundidge, Steven P.,Benigni, Daniel A.,Sapino, Chester
-
-
- Synthesis of the mirror image of the RNA fragment D-CAAGG: A model compound to study interactions between oligonucleotides of opposite handedness
-
The pentamer L-CAAGG was prepared starting from properly protected β-L-ribonucleosides via a phosphotriester approach.The identity and chiral purity of the pentamer were established by 1H NMR and CD spectroscopy, respectively.
- Visser, G. M.,van Westrenen, J.,van Boeckel, C. A. A.,van Boom, J. H.
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p. 528 - 537
(2007/10/02)
-
- A Stereocontrolled Synthesis of 1,3,6-Tri-O-benzoyl-α-D-ribofuranose
-
The synthesis of a valuable carbohydrate intermediate, 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4), has been achieved in a convenient, one-step process from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (7).
- Brodfuehrer, Paul R.,Sapino, Chester,Howell, Henry G.
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p. 2597 - 2598
(2007/10/02)
-
