Tag: 447.2268

Microwave induced synthesis of ribonucleosides on solid support was written by Andrzejewska, Mariola;Kaminski, Jaroslaw;Kazimierczuk, Zygmunt. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2002.Recommanded Product: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate This article mentions the following:

In recent years, there is a growing interest in applying microwave irradiation for the synthesis of organic compounds This study was conducted to test the utility of the microwave-assisted procedure for nucleoside synthesis and to attract attention to the possible use of microwave induced reactions to nucleic acid chem. Our approach was to use the “fusion” method in which the heterocyclic base reacts with the appropriate peracylated sugar at an elevated temperature and a vacuum is applied to remove the acetic acid generated. The best results were obtained when silica gel was used as a solid support phase. As expected, the nucleosides formed were the thermodynamically controlled 1β anomers for benzimidazoles and the 9β anomers for purines. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Recommanded Product: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Recommanded Product: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Nucleic Acid Related Compounds. 118. Nonaqueous Diazotization of Aminopurine Derivatives. Convenient Access to 6-Halo- and 2,6-Dihalopurine Nucleosides and 2′-Deoxynucleosides with Acyl or Silyl Halides was written by Francom, Paula;Robins, Morris J.. And the article was included in Journal of Organic Chemistry in 2003.Category: tetrahydrofurans This article mentions the following:

Treatment of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-chloropurine with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO₂) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside I (R = OAc, X = Y = Cl), and acetyl chloride/BTEA-NO₂ was equally effective (∼85%, without chromatog.). TMS-Br/tert-Bu nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analog I (R = OAc, X = Br, Y = Cl) (85%). (Chloro or bromo)-dediazoniation of 3′,5′-di-O-acetyl-2′-deoxyadenosine gave chloro I (R = X = H, Y = Cl) (63%) or bromo I (R = X = H, Y = Br) (80%) purine deoxynucleosides, and 2′,3′,5′-tri-O-acetyladenosine was converted into the 6-chloropurine nucleoside I (R = OAc, X = H, Y = Cl) (71%). In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Category: tetrahydrofurans).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Category: tetrahydrofurans

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Fluorescent Probes for Ecto-5′-nucleotidase (CD73) was written by Schmies, Constanze C.;Rolshoven, Georg;Idris, Riham M.;Losenkova, Karolina;Renn, Christian;Schaekel, Laura;Al-Hroub, Haneen;Wang, Yulu;Garofano, Francesca;Schmidt-Wolf, Ingo G. H.;Zimmermann, Herbert;Yegutkin, Gennady G.;Mueller, Christa E.. And the article was included in ACS Medicinal Chemistry Letters in 2020.Reference of 3056-18-6 This article mentions the following:

Ecto-5′-nucleotidase (CD73) catalyzes the hydrolysis of AMP to anti-inflammatory, immunosuppressive adenosine. It is expressed on vascular endothelial, epithelial, and also numerous cancer cells where it strongly contributes to an immunosuppressive microenvironment. In the present study we designed and synthesized fluorescent-labeled CD73 inhibitors with low nanomolar affinity and high selectivity based on N⁶-benzyl-α,β-methylene-ADP (PSB-12379) as a lead structure. Fluorescein was attached to the benzyl residue via different linkers resulting in PSB-19416 (14b, K_i 12.6 nM) and PSB-18332 (14a, K_i 2.98 nM) as fluorescent high-affinity probes for CD73. These compounds are anticipated to become useful tools for biol. studies, drug screening, and diagnostic applications. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Reference of 3056-18-6).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Reference of 3056-18-6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Study of the N⁷ Regioselective Glycosylation of 6-Chloropurine and 2,6-Dichloropurine with Tin and Titanium Tetrachloride was written by Tranova, Lenka;Styskala, Jakub. And the article was included in Journal of Organic Chemistry in 2021.Computed Properties of C16H16Cl2N4O7 This article mentions the following:

6-Chloropurine and 2,6-dichloropurine were regioselectively glycosylated at position 7 to give the corresponding peracetylated N⁷-nucleosides, which can be suitable for other purine transformations. In this work, we study the distribution of N⁷/N⁹-isomers produced via the Vorbruggen method under different conditions, using an N-trimethylsilylated purine derivative and SnCl₄ or TiCl₄ as a catalyst. The main effort is devoted to reversing the disadvantageous predominant selectivity of most glycosylation reactions at the N⁹ position and thus to determining conditions that maximize the regioselectivity of glycosylation toward the desired N⁷-isomer. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Computed Properties of C16H16Cl2N4O7).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Computed Properties of C16H16Cl2N4O7

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Protonation Studies of Modified Adenine and Adenine Nucleotides by Theoretical Calculations and ¹⁵N NMR was written by Major, Dan T.;Laxer, Avital;Fischer, Bilha. And the article was included in Journal of Organic Chemistry in 2002.SDS of cas: 3056-18-6 This article mentions the following:

The acid/base character of nucleobases affects phenomena such as self-association, interaction with metal ions, mol. recognition by proteins, and nucleic acid base-pairing. Therefore, the investigation of proton-transfer equilibrium of natural and synthetic nucleos(t)ides is of great importance to obtain a deeper understanding of these phenomena. For this purpose, a set of ATP prototypes was investigated using ¹⁵N NMR spectroscopy, and the corresponding adenine bases were investigated by theor. calculations ¹⁵N NMR measurements provided not only acidity constants but also information on the protonation site(s) on the adenine ring and regarding the ratio of the singly protonated species in equilibrium Substituents of different nature and position on the adenine ring did not change the preferred protonation site, which remained N1. However, for 2-thioether-ATP derivatives a mixed population of N1 and N7 singly protonated species was observed Reduction of basicity of 0.4-1 pK_a units relative to ATP was also observed for all evaluated ATP derivatives, except for 2-Cl-ATP, for which K_a was ∼10,000-fold lower. To explain the substitution-dependent variations in the exptl. pK_a values of the ATP analogs, gas-phase proton affinities (PA), ΔΔG^hyd, and pK_a values of the corresponding adenine bases were calculated using quantum mech. methods. The computed PA and ΔΔG^hyd values successfully explained the exptl. pK_a values. A computational procedure for the prediction of accurate pK_a values was developed using d. functional theory and polarizable continuum model calculations In this procedure, we developed a set of parameters for the polarizable continuum model that was fitted to reproduce exptl. pK_a values of nitrogen heterocycles. This method is proposed for the prediction of pK_a values and protonation site(s) of purine analogs that have not been synthesized or analyzed. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6SDS of cas: 3056-18-6).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.SDS of cas: 3056-18-6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Protonation Studies of Modified Adenine and Adenine Nucleotides by Theoretical Calculations and ¹⁵N NMR was written by Major, Dan T.;Laxer, Avital;Fischer, Bilha. And the article was included in Journal of Organic Chemistry in 2002.SDS of cas: 3056-18-6 This article mentions the following:

The acid/base character of nucleobases affects phenomena such as self-association, interaction with metal ions, mol. recognition by proteins, and nucleic acid base-pairing. Therefore, the investigation of proton-transfer equilibrium of natural and synthetic nucleos(t)ides is of great importance to obtain a deeper understanding of these phenomena. For this purpose, a set of ATP prototypes was investigated using ¹⁵N NMR spectroscopy, and the corresponding adenine bases were investigated by theor. calculations ¹⁵N NMR measurements provided not only acidity constants but also information on the protonation site(s) on the adenine ring and regarding the ratio of the singly protonated species in equilibrium Substituents of different nature and position on the adenine ring did not change the preferred protonation site, which remained N1. However, for 2-thioether-ATP derivatives a mixed population of N1 and N7 singly protonated species was observed Reduction of basicity of 0.4-1 pK_a units relative to ATP was also observed for all evaluated ATP derivatives, except for 2-Cl-ATP, for which K_a was ∼10,000-fold lower. To explain the substitution-dependent variations in the exptl. pK_a values of the ATP analogs, gas-phase proton affinities (PA), ΔΔG^hyd, and pK_a values of the corresponding adenine bases were calculated using quantum mech. methods. The computed PA and ΔΔG^hyd values successfully explained the exptl. pK_a values. A computational procedure for the prediction of accurate pK_a values was developed using d. functional theory and polarizable continuum model calculations In this procedure, we developed a set of parameters for the polarizable continuum model that was fitted to reproduce exptl. pK_a values of nitrogen heterocycles. This method is proposed for the prediction of pK_a values and protonation site(s) of purine analogs that have not been synthesized or analyzed. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6SDS of cas: 3056-18-6).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.SDS of cas: 3056-18-6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem