5-Methyluridine

Base Information

• Chemical Name: 5-Methyluridine
• CAS No.: 1463-10-1
• Deprecated CAS: 849658-09-9
• Molecular Formula: C10H14N2O6
• Molecular Weight: 258.231
• Hs Code.: PRICE
• European Community (EC) Number: 215-973-9
• UNII: ZS1409014A
• DSSTox Substance ID: DTXSID20163348
• Nikkaji Number: J32.354C
• Wikipedia: 5-Methyluridine
• Wikidata: Q425078
• Metabolomics Workbench ID: 37485
• ChEMBL ID: CHEMBL106175
• Mol file: 1463-10-1.mol

Synonyms:5-methyluridine;ribosylthymine;ribothymidine

Chemical Property of 5-Methyluridine

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 183-184 °C(lit.)
• Refractive Index: 1.618
• PKA: 9.55±0.10(Predicted)
• PSA: 124.78000
• Density: 1.576 g/cm³
• LogP: -2.54350
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Sparingly, Sonicated)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 258.08518617
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

5-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: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: 5-Methyluridine is a pyrimidine nucleoside and methylated form of uridine. It is the ribonucleoside counterpart to the deoxyribonucleoside thymidine, which lacks a hydroxyl group at the 2' position. 5-Methyluridine contains a thymine base joined to a ribose pentose sugar. It is an endogenous methylated nucleoside found in human fluids. In cells, 5-methyluridine is present in tRNA, formed during its post-transcriptional modification by the methylation of uridine.
• Uses: A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.It enhances the antitumor activity of 5-fluorouracil in a mouse Erlich solid carcinoma model and a P388 murine leukemia model. It has been used to characterize the activity of a variety of enzymes, including uridine nucleosidase.

Technology Process of 5-Methyluridine

There total 67 articles about 5-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: 98.0%

2',3',5'-tri-O-benzoyluridine (3180-76-5) → 5-Methyluridine (1463-10-1,642082-80-2)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1021/jo00103a017

Reference yield: 95.0%

2',3',5'-tri-O-benzoyluridine (3180-76-5) → benzoic acid ethyl ester (93-89-0,99341-95-4) + benzamide (55-21-0,27208-38-4) + 5-Methyluridine (1463-10-1,642082-80-2)

Guidance literature:

With ammonia; In ethanol; at 20 ℃;

Reference yield: 94.0%

1-(5'-O-trityl-β-D-ribofuranosyl)thymine (101796-28-5) → 5-Methyluridine (1463-10-1,642082-80-2)

Guidance literature:

With carbon tetrabromide; In methanol; at 20 ℃; for 12h; Irradiation;

DOI:10.1016/j.tetlet.2003.10.205

upstream raw materials:

2',3',5'-tri-O-benzoyluridine

5-(hydroxymethyl)uridine

trimethylaluminum

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

Downstream raw materials:

1-[(6aR,8R,9S,9aR)-tetrahydro-9-hydroxy-2,2,4,4-tetraisopropyl-6H-furo[3,2-f]-[1,3,5,2,4]trioxadisilocin-8-yl](5-methylpyrimidine)-2.4(1H_.3H)-dione

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine

2-Acetoxy-2-methyl-propionic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

stavudin

Refernces

• 1、 Zinchenko, A. I.,Barai, V. N.,Bokut', S. B.,Kvasyuk, E. I.,Mikhailopulo, I. A.. "CHEMICAL-ENZYMATIC SYNTHESIS OF 1-(β-D-ARABINOFURANOSYL)THYMINE". . p. 504 - 505. Retrieved 1989.
• 2、 Xie, Li-Jun,Yang, Xiao-Ti,Wang, Rui-Li,Cheng, Hou-Ping,Li, Zhi-Yan,Liu, Li,Mao, Lanqun,Wang, Ming,Cheng, Liang. "Identification of Flavin Mononucleotide as a Cell-Active Artificial N6-Methyladenosine RNA Demethylase". . p. 5028 - 5032. Retrieved 2019.
• 3、 Zhu, Shaozhou,Ren, Lu,Wang, Jianjun,Zheng, Guojun,Tang, Pingwah. "Two-step efficient synthesis of 5-methyluridine via two thermostable nucleoside phosphorylase from Aeropyrum pernix". . p. 2102 - 2104. Retrieved 2012.
• 4、 kari, Vinko,Matuli-Adami, Jasenka. "Synthesis of 5-Methyluridine and Its 5'-Mercapto-, 2-Amino-, and 4',5'-Unsatured Analogues". . p. 2179 - 2186. Retrieved 1980.
• 5、 Adluri, Bharanishashank,Britton, Robert,Campeau, Louis-Charles,Cohen, Ryan,Lehmann, Johannes,Meanwell, Michael,Silverman, Steven M.,Wang, Yang. "A short de novo synthesis of nucleoside analogs". . p. 725 - 730. Retrieved 2020.
• 6、 Alexeev, Cyril S.,Drenichev, Mikhail S.,Dorinova, Evgeniya O.,Esipov, Roman S.,Kulikova, Irina V.,Mikhailov, Sergey N.. "Use of nucleoside phosphorylases for the preparation of 5-modified pyrimidine ribonucleosides". . . Retrieved 2019/11/13.