2'-O-Methyluridine

Base Information

• Chemical Name: 2'-O-Methyluridine
• CAS No.: 2140-76-3
• Molecular Formula: C10H14N2O6
• Molecular Weight: 258.231
• Hs Code.: 29389090
• UNII: 399VZB6TMB
• DSSTox Substance ID: DTXSID10943959
• Nikkaji Number: J120.780F
• Wikidata: Q15632791
• Metabolomics Workbench ID: 53677
• Mol file: 2140-76-3.mol

Synonyms:2'-O-methyluridine;O(2')-methyluridine

Chemical Property of 2'-O-Methyluridine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 154-156 ºC
• PKA: 9.39±0.10(Predicted)
• PSA: 113.78000
• Density: 1.536 g/cm³
• LogP: -2.19780
• Storage Temp.: Store at 0°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 258.08518617
• Heavy Atom Count: 18
• Complexity: 385

Purity/Quality:

98% ^*data from raw suppliers

2''-O-MethylUridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1N2C=CC(=O)NC2=O)CO)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
• Description: 2'-O-Methyluridine is an analog of uridine and has been shown to have antiviral and anticancer properties. 2'-O-Methyluridine inhibits protein synthesis by competing with uridine for the active site of the enzyme ribonucleotide reductase, which converts ribonucleotides to dNMPs. This compound also inhibits RNA synthesis by disrupting the pairing of adenine and cytosine residues in RNA strands.
• Uses: Uridine analog. 2'-O-Methyluridine is used for preparation of antiviral nucleoside derivatives as inhibitors of subgenomic hepatitis C virus RNA replication. Uridine analog. Used for preparation of antiviral nucleoside derivatives as inhibitors of subgenomic hepatitis C virus RNA replication.

Technology Process of 2'-O-Methyluridine

There total 51 articles about 2'-O-Methyluridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1'-(3',5'-O-benzyl-2'-O-methyl-β-D-ribofuranosyl)uracil (156541-83-2) → 2'-O-methyluridine (2140-76-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 0.5h; under 760 Torr;

DOI:10.1016/S0040-4020(01)80693-1

Reference yield: 95.0%

C25H28N2O7 (1384271-34-4) → 2'-O-methyluridine (2140-76-3)

Guidance literature:

With formic acid; palladium on activated charcoal; hydrogen; In water; isopropyl alcohol; for 12h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2012.05.035

Reference yield: 95.0%

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methyluridine (83167-64-0) → 2'-O-methyluridine (2140-76-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

diazomethane

uridine

3-(4-methoxyphenylmethyl)-2'-O-methyluridine

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methyluridine

Downstream raw materials:

C₂₂H₄₂N₂O₆Si₂

1-((2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

2'-O-Methyl-uridin-5'-monophosphat

(5'R)-3'-O-(tert-butyldiphenylsilyl)-5'-C-(tert-butyldimethylsilyloxyethyl)-2'-O-methyluridine

Refernces

• 1、 Hall. "-". . p. 876,878. Retrieved 1964.
• 2、 Schneider, Christina,Becker, Sidney,Okamura, Hidenori,Crisp, Antony,Amatov, Tynchtyk,Stadlmeier, Michael,Carell, Thomas. "Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations". supporting information. p. 5943 - 5946. Retrieved 2018/04/30.
• 3、 Aleiwi, Bilal A.,Kurosu, Michio. "A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen". experimental part. p. 3758 - 3762. Retrieved 2012/09/25.