7481-90-5

Basic information

• Product Name: 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE
• Synonyms: 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE;1-(3,5-Anhydro-2-deoxy-β-D-threo-pentofuranosyl)thyMine
• CAS NO: 7481-90-5
• Molecular Formula: C₁₀H₁₂N₂O₄
• Molecular Weight: 224.21
• Product Categories: Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
• Mol File: 7481-90-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 196 °C
• Appearance: /
• Density: 1.412g/cm³
• Refractive Index: -126 ° (C=1, 1mol/L NaOH)
• PKA: 9.52±0.10(Predicted)
• CAS DataBase Reference: 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE(7481-90-5)
• EPA Substance Registry System: 1-(3,5-ANHYDRO-2-DEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE(7481-90-5)

Safety Data

• Hazardous Substances Data: 7481-90-5(Hazardous Substances Data)

Usage

General Description

1-(3,5-anhydro-2-deoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione is a chemical compound that is a derivative of the nucleoside thymidine. It is composed of a pyrimidine base and a deoxyribose sugar, and it has the additional modification of a 3,5-anhydro group on the sugar ring. This chemical compound is commonly used in the synthesis and study of nucleoside and nucleotide analogs, particularly in the field of medicinal chemistry and drug development. Its structure and properties make it useful for investigating the interactions and mechanisms of action of nucleoside analogs in biological systems, as well as their potential as antiviral or anticancer agents.

InChI:InChI=1/C10H12N2O4/c1-5-3-12(10(14)11-9(5)13)8-2-6-7(16-8)4-15-6/h3,6-8H,2,4H2,1H3,(H,11,13,14)

Upstream product

• 63914-08-9 3',5'-bis-O-(p-tolylsulfonyl)thymidine 
• 6979-97-1 3',5'-diacetylthymidine 
• 452-51-7 D-2-deoxyribose 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 
• 50-89-5 thymidine 
• 56822-33-4 3',5'-di-O-mesylthymidine 

Downstream Products

• 186692-51-3 C₁₀H₁₁N₂O₄^(1-)*K⁽¹⁺⁾ 
• 142409-84-5 1-[(2R,4R,5S)-5-Iodomethyl-4-(9-phenyl-9H-xanthen-9-yloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 142409-87-8 (1R,10R,11R)-4-Methyl-11-(9-phenyl-9H-xanthen-9-yloxy)-8,13-dioxa-2,6-diaza-tricyclo[8.2.1.0^2,7]trideca-3,6-dien-5-one 
• 142409-89-0 3'-Deoxy-3'-(phenylthio)thymidine 
• 142409-90-3 1-((2R,4R,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 117901-57-2 1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine 
• 131933-44-3 1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine 
• 15981-92-7 2,3'-anhydrothymidine 
• 500018-98-4 2'-deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-3'-O-benzoyl-2',5'-dideoxythymidine 
• 500018-88-2 benzoic acid 2-[2-({[5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-hydroxy-methyl}-ethoxy-phosphinoyl)-ethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 500018-90-6 Benzoic acid (2R,3S,5R)-2-(2-{[(2S,3S,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-ethoxy-phosphinoyl}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 500018-87-1 C₄₇H₅₇N₄O₁₂PSi 
• 500018-89-3 C₄₇H₅₇N₄O₁₁PSi 
• 500018-99-5 2'-Deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-2',5'-dideoxythymidine 

Relevant articles and documents

SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG

The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.

The synthesis and NMR investigation on novel boron derivatives of stavudine

Preparation and spectroscopic properties of novel boron-containing derivatives of anti-HIV agent stavudine are presented, The new compounds, (5′-O-(4,4,5,5-tetramethyl-1,3,2-dioxaboronate)-2′-3′-didehydro-2′-3′-dideoxythymidine and 5′-O-(dihydroxyboronate)-2′-3′-didehydro-2′-3′-dideoxythymidine), were prepared by direct reaction between stavudine and reagents containing B{single bond}H moieties - pinacolborane and borane-dimethylsulfide complexes, respectively. The boron coordination equilibrium of those compounds was analyzed by water titration monitored by NMR. Results of the DFT calculations and NMR experiments pointed to structural and electronic similarity of tetrahedral boron complexes to phosphate group.

Simple and efficient method for the synthesis of 2′,3′-didehydro-3′-deoxythymidine (d4T)

2′,3′-Didehydro-3′-deoxythymidine (d4T) is an orally active antiviral drug used in the treatment of AIDS. A novel two-step synthetic method was developed for the synthesis of d4T using inexpensive reagents. An improvement in the yield was achieved for the conversion of the intermediate oxetane to d4T. This is the first simple and efficient method for the large-scale synthesis of d4T.