69256-17-3

Basic information

• Product Name: 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• Synonyms: 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;2'-Fluoro-5-methylarabinosyluracil;2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-;2'-Fluoro-5-methyl-1--D-arabinofuranosyluracil;1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyluracil;1-(2-Fluoro-2-deoxy-β-D-arabinofuranosyl)thymine;5-Methyl-1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)uracil
• CAS NO: 69256-17-3
• Molecular Formula: C₁₀H₁₃FN₂O₅
• Molecular Weight: 260.22
• EINECS: 200-001-2
• Mol File: 69256-17-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.55 g/cm3
• Storage Temp.: 2-8°C
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione(69256-17-3)
• EPA Substance Registry System: 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione(69256-17-3)

Safety Data

• Hazardous Substances Data: 69256-17-3(Hazardous Substances Data)

Usage

Description

2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil is the impurity of antiviral drug Clevudine (C574150), which is used for the treatment of Hepatitis B.

Uses

2''-Fluoro-5-methyl-1-β-D-arabinofuranosyluracil is the impurity of antiviral drug Clevudine (C574150), which is used for the treatment of Hepatitis B.

Upstream product

• 69124-04-5 1-(3-O-Acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 65-71-4 thymin 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 83966-95-4 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylcytosine 
• 84025-00-3 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose 
• 56632-81-6 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 
• 554-01-8 5-methylcytosin 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 97614-47-6 1-(3',5'-di-O-benzoyl-2'-fluoro-2'-deoxy-α/β-D-arabinofuranosyl)thymine 
• 78636-53-0 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylcytosine 
• 97614-47-6 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine 

Downstream Products

• 128114-97-6 1-(2-deoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 128114-99-8 2,3'-anhydro-1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)thymine 
• 128496-21-9 1-(3-deoxy-2,3-didehydro-2-fluoro-5-O-trityl-β-D-glycero-2-enopentofuranosyl)thymine 
• 132776-23-9 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)-5-methylcytosine 
• 132776-20-6 1-(5-O-benzoyl-2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)thymine 
• 132776-22-8 1-(5-O-benzoyl-2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)-4-thiothymidine 
• 132776-19-3 2,3'-anhydro-1-(5-O-benzoyl-2-deoxy-2-fluoro-D-lyxofuranosyl)thymine 
• 132776-21-7 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)thymine 
• 144822-48-0 5′-O-(dimethoxytrityl)-2′-β-fluorothymidine 
• 1054490-12-8 C₂₉H₃₉FN₂O₁₂S 
• 1383974-91-1 (5S,6R)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine 
• 1383974-97-7 (5R,6S)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine 
• 1383974-90-0 3',5'-di-O-trityl-2'-arabinofluorothymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Relevant articles and documents

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

NEIL1 Binding to DNA Containing 2'-Fluorothymidine Glycol Stereoisomers and the Effect of Editing

Thymine glycol (Tg), one of the oxidized bases formed in DNA by reactive oxygen species, is repaired by the DNA glycosylases such as NEIL1, NTH1 and Endo III. In our recent studies, we showed that NEIL1's catalytic efficiency and lesion specificity are regulated by an RNA-editing adenosine deamination reaction. In this study, we synthesized oligodeoxynucleotides containing 2'-fluorothymidine glycol with either ribo or arabino configuration and investigated the binding of these modified DNAs with the unedited and edited forms of human NEIL1 along with E. coli Endo III. For the two forms of hNEIL1, binding affinities to FTg-containing DNA were similar indicating that the editing effect is more subtle than to simply alter substrate affinity. While the NEIL1-binding to FTg-containing DNAs was largely insensitive to C5 and 2' stereochemistry, a preference was observed for the FTg-G pair over the FTg-A pair. In addition, we found that optimal binding is observed with Endo III and duplex DNA with riboFTg(5S) paired with dG. The modified DNAs reported here will provide useful tools for further characterizing the interaction between DNA repair glycosylases and thymine glycol containing DNA.

A general synthesis of 2′-deoxy-2′-[18F]fluoro-1-β-D- arabinofuranosyluracil and its 5-substituted nucleosides

Several 2′-deoxy-2′-[18F]fluoro-1-β-D- arabinofuranosyluracil derivatives have been synthesized. Coupling of 1-bromo-2-deoxy-2-[18F]fluoro-3,5-di-O-benzoyl-α-D- arabinofuranose 2 with protected uracil derivatives 3a-e followed by hydrolysis and high-performance liquid chromatography purification produced the radiolabeled nucleosides 4a-e in 15-30% yield (d. c.), > 99% radiochemical purity and 55.5-103.6 GBq/μmol specific activities. Copyright