200435-92-3

Basic information

• Product Name: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione
• Synonyms: 1-(2'-O,4-C-Methylene-beta-D-ribofuranosyl)uridine;1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione;1-(2'-O 4-C-Methylene-b-D-ribofuranosyl)uridine;1-(2'-O, 4-C-Methylene-β-D- ribofuranosyl)uridine;1-[2,5-Anhydro-4-(hydroxymethyl)-α-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione;2'-O,4'-C-Methyleneuridine
• CAS NO: 200435-92-3
• Molecular Formula: C₁₀H₁₂N₂O₆
• Molecular Weight: 256.213
• Mol File: 200435-92-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 239-243 °C(Solv: methanol (67-56-1))
• Appearance: /
• Density: 1.695
• PKA: 9.30±0.10(Predicted)
• CAS DataBase Reference: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione(200435-92-3)
• EPA Substance Registry System: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione(200435-92-3)

Safety Data

• Hazardous Substances Data: 200435-92-3(Hazardous Substances Data)

Usage

Uses

2''-?O,?4''-?C-?Methyleneuridine is bridged nucleic acid which displays high binding affinities to DNA and RNA when paired with a phenoxazine base.

Upstream product

• 206055-63-2 (1S,3R,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 195705-15-8 4'-(p-toluenesulfonyl)oxymethyluridine 
• 200435-89-8 3'-O-benzyl-4'-(p-toluenesulfonyloxymethyl)uridine 
• 63592-89-2 O^2'_,O3'-cyclohexane-1,1-diyl-4'-hydroxymethyl-uridine 
• 1094603-23-2 ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate 
• 1094603-22-1 ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate 
• 1094603-21-0 (2R,3R,4S)-4-(benzyloxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate 
• 293751-03-8 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 293751-01-6 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 1174917-62-4 C₂₆H₃₀N₂O₆Si 
• 1174917-61-3 C₃₇H₃₈N₂O₆Si 
• 1174917-60-2 C₄₀H₄₄N₂O₁₀SSi 
• 1314716-21-6 C₃₈H₄₄O₁₀SSi 
• 200435-91-2 1-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 206055-67-6 (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 206055-71-2 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione 
• 206055-75-6 (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane 
• 206055-76-7 5′-O-(4,4′-dimethoxytrityl)-2′-O,4′-C-methylenethymidine-3′-[O-(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite 
• 1314716-25-0 C₃₄H₃₁N₃O₈S 
• 1314716-26-1 C₄₃H₄₈N₅O₉PS 
• 1314716-27-2 C₄₀H₄₅N₃O₈SSi 
• 1314716-28-3 C₄₇H₅₀N₄O₈SSi 
• 1314716-29-4 C₄₁H₃₆N₄O₈S 
• 1314716-30-7 C₅₀H₅₃N₆O₉PS 
• 1275611-00-1 (1R,3R,4R,7S)-3-[5-(3-benzoyloxypropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane 

Relevant articles and documents

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.

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