5-Methylaminomethyluridine

Base Information

• Chemical Name: 5-Methylaminomethyluridine
• CAS No.: 72667-55-1
• Molecular Formula: C₁₁H₁₇N₃O₆
• Molecular Weight: 287.272
• DSSTox Substance ID: DTXSID60559468
• Metabolomics Workbench ID: 53777
• Nikkaji Number: J1.484.902E
• Wikidata: Q27109321
• Mol file: 72667-55-1.mol

Synonyms:5-methylaminomethyluridine;5-MNM-U

Chemical Property of 5-Methylaminomethyluridine

Chemical Property:

• PSA: 137.07000
• LogP: -2.32930
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 287.11173527
• Heavy Atom Count: 20
• Complexity: 440

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CNCC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

Technology Process of 5-Methylaminomethyluridine

There total 8 articles about 5-Methylaminomethyluridine 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: 90.0%

C16H25N3O7 → 5-methylaminomethyluridine (72667-55-1)

Guidance literature:

With methylamine; In water; at 60 ℃; for 1h;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield: 90.0%

5-pivaloyloxymethyluridine + methylamine (74-89-5) → 5-methylaminomethyluridine (72667-55-1)

Guidance literature:

In ethanol; at 60 ℃; for 1h; Solvent; Time;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 5-methylaminomethyluridine (72667-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) NH₃, 3.) Dowex H⁺ / 2.) methanol

2: H₂O₂, 4N NaOH

With sodium hydroxide; Dowex H⁺; ammonia; dihydrogen peroxide;

DOI:10.1021/ja00257a044

upstream raw materials:

2-thio-5-<(methylamino)methyl>uridine

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2',3'-O-isopropylidene-5-hydroxymethyl-uridine

methylamine

Refernces

• 1、 Bartosik, Karolina,Leszczynska, Grazyna. "Synthesis of various substituted 5-methyluridines (xm5U) and 2-thiouridines (xm5s2U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine". . p. 6593 - 6597. Retrieved 2015/11/09.