5-Methoxyuridine

Base Information

• Chemical Name: 5-Methoxyuridine
• CAS No.: 35542-01-9
• Molecular Formula: C10H14 N2 O7
• Molecular Weight: 274.23
• Hs Code.: 29349990
• European Community (EC) Number: 252-609-8
• Nikkaji Number: J260.644E
• Metabolomics Workbench ID: 53774
• Mol file: 35542-01-9.mol

Synonyms:5-methoxyuridine

Chemical Property of 5-Methoxyuridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 8?+-.0.10(Predicted)
• Flash Point: °C
• PSA: 134.01000
• Density: 1.65g/cm³
• LogP: -2.84330
• Storage Temp.: −20°C
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 274.08010079
• Heavy Atom Count: 19
• Complexity: 424

Purity/Quality:

97% ^*data from raw suppliers

5-Methoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: COC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: 5-Methoxyuridine is an intermediate in the biosynthesis of pyrimidines and is also used as a precursor for other compounds. 5-Methoxyuridine is an analog of Uridine and is used as a reagent in the synthesis of 5-OMe-UDP, a potent and selective P2Y6-receptor agonist. 5-Methoxyuridine inhibits messenger RNA (mRNA) production in bacteria by interfering with sequence recognition and binding sites within the ribosome and preventing.
• Uses: 5-Methoxyuridine is an analog of Uridine (U829910) and is used as a reagent in the synthesis of 5-OMe-UDP, a potent and selective P2Y6-receptor agonist.

Technology Process of 5-Methoxyuridine

There total 6 articles about 5-Methoxyuridine 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:

2′,3′,5′-tri-O-acetyl-5-methoxyuridine → 5-methoxycarbonylmethyl-2'-O-methyl-uridine (35542-01-9)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

Reference yield:

triethylamine carbonate (15715-58-9) + bis(tri-n-butylammonium) pyrophosphate (5975-18-8,50859-18-2,55612-36-7,88499-44-9,103659-66-1) → 5-methoxycarbonylmethyl-2'-O-methyl-uridine (35542-01-9)

Guidance literature:

With tributyl-amine; trichlorophosphate;

Reference yield:

1,2,3,5-tetra-O-acetyl-D-ribofuranose (28708-32-9) → 5-methoxycarbonylmethyl-2'-O-methyl-uridine (35542-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,O-bis(trimethylsilane)acetamide / acetonitrile / 20 °C

1.2: 0 - 20 °C

2.1: ammonia / methanol / 20 °C

With ammonia; N,O-bis(trimethylsilane)acetamide; In methanol; acetonitrile;

upstream raw materials:

triethylamine carbonate

bis(tri-n-butylammonium) pyrophosphate

2-thio-5-methoxyuridine

5-methoxyuridine 2',3',5'-tri-O-benzoate

Refernces

• 1、 -. "Methotrexate adjuvants to reduce toxicity and methods for using the same". . . Retrieved 2016/08/10.
• 2、 Bartos, Paulina,Ebenryter-Olbinska, Katarzyna,Sochacka, Elzbieta,Nawrot, Barbara. "The influence of the C5 substituent on the 2-thiouridine desulfuration pathway and the conformational analysis of the resulting 4-pyrimidinone products". supporting information. p. 5587 - 5594. Retrieved 2015/11/11.