Chmu-methyl ester

Base Information

• Chemical Name: Chmu-methyl ester
• CAS No.: 89665-83-8
• Molecular Formula: C₁₂H₁₆N₂O₉
• Molecular Weight: 332.267
• DSSTox Substance ID: DTXSID201008938
• Mol file: 89665-83-8.mol

Synonyms:5-(carboxy(hydroxy)methyl)uridine methyl ester;CHMU-methyl ester

Chemical Property of Chmu-methyl ester

Chemical Property:

• PSA: 171.57000
• Density: 1.687g/cm³
• LogP: -3.23320
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 332.08558009
• Heavy Atom Count: 23
• Complexity: 549

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC(=O)C(C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: 5-(Carboxyhydroxymethyl)uridine Methyl Ester is a naturally occurring modified nucleoside.

Technology Process of Chmu-methyl ester

There total 8 articles about Chmu-methyl ester 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: 86.0%

methanol (67-56-1) + 5-(ethoxycarbonyl)(hydroxy)methyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine (1261157-41-8) → (S)-5-methoxycarbonylhydroxymethyluridine (89665-83-8)

Guidance literature:

With hydrogenchloride; at 20 ℃;

DOI:10.1002/anie.201001242

Reference yield: 50.0%

methanol (67-56-1) + 5-carboxyhydroxymethyluridine (934743-11-0) → (S)-5-methoxycarbonylhydroxymethyluridine (89665-83-8) + 5-(R-methoxycarbonyl)(hydroxy)methyl-uridine (89665-84-9)

Guidance literature:

methanol; 5-carboxyhydroxymethyluridine; With hydrogenchloride; at 20 ℃; for 2h;

Resolution of racemate;

DOI:10.1039/c9ra08548c

Reference yield:

2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine (60170-16-3) → (S)-5-methoxycarbonylhydroxymethyluridine (89665-83-8) + 5-(R-methoxycarbonyl)(hydroxy)methyl-uridine (89665-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / acetonitrile / 2 h / 20 °C

2.1: hydrogenchloride / 2 h / 5 °C

3.1: water / 2 h / 5 °C

3.2: Ascentis C₁₈ / Resolution of racemate

With hydrogenchloride; water; triethylamine; In acetonitrile; 2.1: |Pinner Amidine Synthesis;

DOI:10.1039/c9ra08548c

upstream raw materials:

methanol

5-(ethoxycarbonyl)(hydroxy)methyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine

5-carboxyhydroxymethyluridine

Refernces

• 1、 Fu, Ye,Dai, Qing,Zhang, Wen,Ren, Jin,Pan, Tao,He, Chuan. "The AlkB domain of mammalian ABH8 catalyzes hydroxylation of 5-methoxycarbonylmethyluridine at the wobble position of tRNA". supporting information; experimental part. p. 8885 - 8888. Retrieved 2011/02/23.