122567-97-9 | Pyrimidines

Crich, David’s team published research in Tetrahedron in 1998 | CAS: 122567-97-9

((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Related Products of 122567-97-9

Crich, David; Yao, Qingwei published an article on January 15 ,1998. The article was titled 《Free radical chemistry of nucleosides and nucleotides Ring opening of C4′-radicals》, and you may find the article in Tetrahedron.Related Products of 122567-97-9 The information in the text is summarized as follows:

It is demonstrated that nucleotide C4′ radicals may be generated from a C4′-thioester on treatment with tributyltin hydride. When the reaction is conducted in benzene at reflux the C4′ radical expels the C3′-phosphate group to give a radical cation. This species undergoes deprotonation to an allylic radical which suffers cleavage of the deoxyribose ring. Similar reactions are observed when the reaction is conducted with tris(trimethylsilyl)silane in place of the stannane. In methanolic benzene the radical cation is trapped by methanol to give a new C4′ radical which is quenched before ring opening. The behavior of C4′ radicals toward ring opening is discussed in terms of the conformations imposed by the substituents at C3′. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Related Products of 122567-97-9)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Kawakami, Hiroshi’s team published research in Heterocycles in 1991 | CAS: 122567-97-9

Kawakami, Hiroshi; Ebata, Takashi; Koseki, Koshi; Matsumoto, Katsuya; Matsushita, Hajime; Naoi, Yoshitake; Itoh, Kazuo published their research in Heterocycles on December 1 ,1991. The article was titled 《Synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides utilizing coupling reactions between nucleic bases and phenylthio-substituted 2,3-dideoxyribose》.Formula: C17H16N2O5 The article contains the following contents:

Stereoselectivities in coupling reactions between silylated pyrimidine bases I (X = O, R = H, Me; X = NAc, R = H) and 3- or 2-α-phenylthio-2,3-dideoxyribose derivatives, e.g., II (R1 = Cl, OAc) and III, resp., was examined In the former case, no stereoselectivities were observed when the coupling reactions were performed either with 1-chloro sugar in an SN2 mode or in the presence of Lewis acids as catalyst in an SN1 mode. Coupling reaction with 2-α-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of nucleosides, e.g. IV, α:β = 1:9. All these nucleosides were converted to 2′,3′-didehydro-2′,3′-dideoxynucleosides, such as V, by oxidation to sulfoxides followed by thermal elimination of sulfenic acid. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Formula: C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chen, Bang-Chi’s team published research in Tetrahedron Letters in 1998 | CAS: 122567-97-9

Chen, Bang-Chi; Quinlan, Sandra L.; Reid, J. Gregory; Spector, Richard H. published an article on February 19 ,1998. The article was titled 《A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates》, and you may find the article in Tetrahedron Letters.Formula: C17H16N2O5 The information in the text is summarized as follows:

The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved byproduct thymine from the readily available ribonucleoside 5-methyluridine. This was accomplished by using a new strategy which involved a regio/stereo controlled β-elimination of trans-bromoacetates. The experimental process involved the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Formula: C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chen, Bang-Chi’s team published research in Tetrahedron Letters in 1995 | CAS: 122567-97-9

Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoateOn October 30, 1995 ,《5′-Benzoyl-2’α-bromo-3′-O-methanesulfonylthymidine: a superior nucleoside for the synthesis of the anti-AIDS drug D4T (stavudine)》 was published in Tetrahedron Letters. The article was written by Chen, Bang-Chi; Quinlan, Sandra L.; Stark, Derron R.; Reid, J. Gregory; Audia, Vicki H.; George, Jacqueline G.; Eisenreich, Emerich; Brundidge, Steve P.; Racha, Saibaba; Spector, Richard H.. The article contains the following contents:

The anti-AIDS drug d4T is prepared in 75% overall yield starting from the readily available ribonucleoside 5-methyluridine. The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate I, which affords d4T without nucleoside bond cleavage. A facile procedure for the deprotection/isolation of this highly water soluble product is also described. After reading the article, we found that the author used ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Becouarn, Stefan’s team published research in Nucleosides & Nucleotides in 1995 | CAS: 122567-97-9

《Efficient transformation of thymidine into 2′,3′-didehydro-2′,3′-dideoxythymidine (D4T) involving opening of a 2,3′-anhydro derivative by phenylselenol》 was written by Becouarn, Stefan; Czernecki, Stanislas; Valery, Jean-Marc. Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate And the article was included in Nucleosides & Nucleotides on August 31 ,1995. The article conveys some information:

A high-yielding method for the introduction of the phenylselenyl residue at the 3′-position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5′. Further oxidation-elimination sequence followed by basic deprotection afforded D4T in 67.5% overall yield from thymidine. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Kumamoto, Hiroki’s team published research in Journal of Organic Chemistry in 2002 | CAS: 122567-97-9

Electric Literature of C17H16N2O5On May 31, 2002, Kumamoto, Hiroki; Tanaka, Hiromichi published an article in Journal of Organic Chemistry. The article was 《Simple Entry to 3′-Substituted Analogues of Anti-HIV Agent Stavudine Based on an Anionic O → C Stannyl Migration》. The article mentions the following:

Reaction of 5′-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3′ and H-2′). When the lithiation of the 5′-O-tert-butyldiphenylsilyl derivative I was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3′-C-silylated product II. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogs variously substituted at the 3′-position by manipulating the 3′-C-stannyl d4T as a common intermediate. In the experiment, the researchers used many compounds, for example, ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Electric Literature of C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Alvarez de Cienfuegos, Luis’s team published research in Tetrahedron Letters in 2005 | CAS: 122567-97-9

Alvarez de Cienfuegos, Luis; Mota, Antonio J.; Rodriguez, Concepcion; Robles, Rafael published an article on January 17 ,2005. The article was titled 《Highly efficient synthesis of 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′,3′-trans-elimination. From iodomethylcyclopropanes to thiirane analogs》, and you may find the article in Tetrahedron Letters.Electric Literature of C17H16N2O5 The information in the text is summarized as follows:

Taking into account the thiophilic properties of iodine, a very simple methodol. to achieve 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides in high yield was performed, using mild, and inexpensive conditions, by means of the treatment of 2′-deoxy-3′,5′-dibenzoyl-2′-iodo-β-nucleoside derivatives with NaHS. The process has shown to be highly dependent of the relative geometry between the iodine atom and the adjacent leaving group. In this way, different essays carried out with pyranose derivatives have concluded in no reaction when the vicinal groups to eliminate do not adopt a trans-diaxial disposition. In addition, the treatment of 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid di-Et ester under the same conditions softly and readily leads to the obtention of a mixture of the expected 2-allyl-malonic acid di-Et ester (as the minor product) and the thiirane derivative 2-thiiranylmethyl-malonic acid di-Et ester (as the major product). In this case, the responsible of the reaction progress are the nucleophilic properties of the sulfur atom rather than the thiophilic character of the iodine atom. The results came from multiple reactions, including the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Electric Literature of C17H16N2O5)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Palomino, Eduardo’s team published research in Journal of Medicinal Chemistry in 1990 | CAS: 122567-97-9

Palomino, Eduardo; Meltsner, Bernard R.; Kessel, David; Horwitz, Jerome P. published an article on January 31 ,1990. The article was titled 《Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS – associated neurological disorders》, and you may find the article in Journal of Medicinal Chemistry.Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate The information in the text is summarized as follows:

Oxygen-sulfur exchange at the C-4 carbonyl of several modified pyrimidine nucleosides, including 3′-azido-3′-deoxythymidine (AZT), is described in an effort to enhance the lipophilicity and, thereby, the delivery to the central nervous system of the sulfur analogs without compromising the anti-HIV activities of the parental structures. Preparation of 3′-azido-3′-deoxy-4-thiothymidine (I) proceeded from 4-thiothymidine and utilized the same methodol. developed for the initial synthesis of AZT. Thiation of 2′,3′-didehydro-3′-deoxythymidine and 2′,3′-didehydro-2′,3′-dideoxyuridine was carried out with Lawesson’s reagent on the corresponding 5′-O-benzoate esters. The products on alk. hydrolysis gave 2′,3′-didehydro-3′-deoxy-4-thiothymidine and 2′,3′-didehydro-2′,3′-dideoxy-4-uridine (III). The same series of reactions were applied to the 5′-O-benzoate esters of 2′,3′-dideoxyuridine and 3′-deoxythymidine to give 2′,3′-dideoxy-4-thiouridine (IV) and 3′-deoxy-4-thiothymidine (V). Characterization of the saturated and unsaturated thionucleosides included mass spectrometric studies. Under electron impact conditions, the thiated analogs gave more intense parent ions than the corresponding oxygen precursors. The lipophilicity of thymidine and the 3′-deoxythymidine derivatives are enhanced significantly, as indicated, by increases in corresponding P values (1-octanol-0.1M sodium phosphate) upon replacement of the 4-carbonyl oxygens by sulfur. II, III, IV, and V were evaluated for their effects on HIV-induced cytopathogenicity of MT-2 and CEM cells. Only II and V were moderately active in protecting both cell lines against the cytolytic effect of HIV. The inhibitory effects of II-V on thymidine phosphorylation by rabbit thymus thymidine kinase were evaluated. Only I showed moderate affinity (Ki = 54 μM) for the enzyme. The generally weak anti-HIV activities of the remaining thio analogs are consistent with correspondingly low susceptibilities to thymidine kinase phosphorylation as estimated from the resp. Ki values of the synthetic nucleosides. However, the phosphorylation of the 5′-monophosphate derivatives to their resp. 5′-triphosphates must also be considered in connection with the weak in vitro anti-HIV effects of these thiated compounds The experimental process involved the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sagandira, Cloudius R.’s team published research in Journal of Organic Chemistry in 2021 | CAS: 122567-97-9

Recommanded Product: 122567-97-9On October 15, 2021 ,《Multistep Continuous Flow Synthesis of Stavudine》 was published in Journal of Organic Chemistry. The article was written by Sagandira, Cloudius R.; Akwi, Faith M.; Sagandira, Mellisa B.; Watts, Paul. The article contains the following contents:

Herein, we demonstrate an elegant multistep continuous flow synthesis for stavudine (d4T), a potent nucleoside chemotherapeutic agent for human immunodeficiency virus, acquired immunodeficiency syndrome (AIDS) and AIDS-related conditions. This was accomplished via six chem. transformations in five sequential continuous flow reactors from an affordable starting material, 5-methyluridine. In the first instance, single step continuous flow synthesis was demonstrated with an average of 97% yield, 21.4 g/h throughput per step, and a total of 15.5 min residence time. Finally, multistep continuous flow synthesis of d4T in 87% total yield with a total residence time of 19.9 min and 117 mg/h throughput without intermediate purification was demonstrated. In the part of experimental materials, we found many familiar compounds, such as ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Recommanded Product: 122567-97-9)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Tortolani, David R.’s team published research in Journal of Pharmaceutical Sciences in 1994 | CAS: 122567-97-9

HPLC of Formula: 122567-97-9On March 31, 1994, Tortolani, David R.; Russell, John W.; Whiterock, Valerie J.; Hitchcock, Michael J. M.; Ghazzouli, Ismail; Martin, John C.; Mansuri, Muzammil M.; Starrett, John E. Jr. published an article in Journal of Pharmaceutical Sciences. The article was 《Prodrugs of 2′,3′-Didehydro-3′-deoxythymidine (D4T): Synthesis, Antiviral Activity, and Rapid Pharmacokinetic Evaluation》. The article mentions the following:

A series of 5′-derivatives and modified pyrimidine analogs of 2′,3′-didehydro-3′-deoxythymidine (d4T, stavudine) were synthesized to determine their potential as oral prodrugs of d4T. Utilizing a screen developed for the rapid evaluation of a variety of prodrugs in mice, it was determined that 5′-acetate provided comparable plasma levels of d4T after oral administration of the prodrug to that when d4T was administered alone. The relative oral bioavailability of methoxy acetate and cyclohexyl carbonate derivatives was 79 and 41%, resp. The dihydropyridine ester did not provide detectable levels of d4T up to 1 h after oral administration of 6. Thiopyrimidine and aminopyrimidine derivatives also failed to provide measurable levels of d4T after oral administration. 5′-Derivatives showed similar activity to that of d4T against HIV and MuLV, as did 5′-benzoyl-4-thio derivative However, the corresponding 4-thio 5′-alc. derivative was inactive. In the experimental materials used by the author, we found ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9HPLC of Formula: 122567-97-9)

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia