52783-53-6Relevant articles and documents
Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose
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, (2020/08/18)
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.
2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations
Abou-Elkhair, Reham A. I.,Wasfy, Abdalla A.,Mao, Song,Du, Jinxi,Eladl, Sobhy,Metwally, Kamel,Hassan, Abdalla E. A.,Sheng, Jia
, p. 19650 - 19662 (2020/12/05)
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
Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
Mohammed, Mohsin O.,Al Dulayymi, Juma'a R.,Baird, Mark S.
supporting information, p. 36 - 42 (2016/11/25)
An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.
Magnesium pyrophosphates in enzyme mimics of nucleotide synthases and kinases and in their prebiotic chemistry
Gopinath, Purushothaman,Ramalingam, Vijayakumar,Breslow, Ronald
, p. 12011 - 12014 (2015/10/12)
Derivatives of ribosyl pyrophosphate have been synthesized, and examined with magnesium salts in the coupling of the ribose unit to various nucleophiles, including pyrazole and 2-chloroimidazole. Only with the magnesium salt present did they generate the ribosyl cation by binding to the leaving group and then couple the ribose derivative with nucleophiles. The role of magnesium salts in phosphorylation of methanol by ATP was also examined. Here a remarkable effect was seen: phosphorylation by ATP was slowed with low concentrations of Mg2+ but accelerated by higher concentrations. Related effects were also seen in the effect of Mg2+ on phosphorylation by ADP. The likely mechanisms explain these effects.
Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis
Thadke, Shivaji A.,Mishra, Bijoyananda,Hotha, Srinivas
supporting information, p. 2466 - 2469 (2013/06/27)
Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.
Automated solid phase synthesis of oligoarabinofuranosides
Kandasamy, Jeyakumar,Hurevich, Mattan,Seeberger, Peter H.
supporting information, p. 4453 - 4455 (2013/06/26)
Automated solid phase synthesis enables rapid access to the linear and branched arabinofuranoside oligosaccharides. A simple purification step is sufficient to provide the conjugation ready oligosaccharides in good yield.
Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides
Ramamurty, Changalvala V. S.,Ganney, Parimala,Rao, C. Srinivas,Fraser-Reid, Bert
supporting information; experimental part, p. 2245 - 2247 (2011/05/17)
The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.
A one-pot synthesis of 1-α- and 1-β-d-arabinofuranosyl-2- nitroimidazoles: Synthons to the markers of tumor hypoxia
Naimi, Ebrahim,Kumar, Piyush,McEwan, Alexander J. B.,Wiebe, Leonard I.
, p. 173 - 178 (2007/10/03)
1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of α-and β-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabi
Synthesis and biological evaluation of novel apio nucleosides with thiazole-4-carboxamide and 1,2,4-triazole-3-carboxamide
Kim, Myong Jung,Jeong, Lak Shin,Kim, Joong Hyup,Shin, Ji Hye,Chung, Soon Yong,Lee, Sang Kook,Chun, Moon Woo
, p. 715 - 724 (2007/10/03)
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.
Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine
Sinha, Sarika,Srivastava, Richa,De Clercq, Erik,Singh, Ramendra K.
, p. 1815 - 1824 (2007/10/03)
Different arabinosides and ribosides, viz. Ara-DDA or 9(1-β-D- arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-β-D- arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or 1(1-β-D- arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-β-D-