5-(1-Methoxy-2-iodoethyl)uridine

Base Information

• Chemical Name: 5-(1-Methoxy-2-iodoethyl)uridine
• CAS No.: 123881-97-0
• Molecular Formula: C₁₂H₁₇IN₂O₇
• Molecular Weight: 428.181
• DSSTox Substance ID: DTXSID30924624
• Nikkaji Number: J273.487G
• Mol file: 123881-97-0.mol

Synonyms:5-(1-Methoxy-2-iodoethyl)uridine;Uridine, 5-(2-iodo-1-methoxyethyl)-;123881-98-1;123881-97-0;DTXSID30924624;4-Hydroxy-5-(2-iodo-1-methoxyethyl)-1-pentofuranosylpyrimidin-2(1H)-one;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(2-iodo-1-methoxy-ethyl)pyrimidine-2,4-dione

Chemical Property of 5-(1-Methoxy-2-iodoethyl)uridine

Chemical Property:

• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 428.00805
• Heavy Atom Count: 22
• Complexity: 486

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(CI)C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: COC(CI)C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

Technology Process of 5-(1-Methoxy-2-iodoethyl)uridine

There total 5 articles about 5-(1-Methoxy-2-iodoethyl)uridine 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: 81.0%

methanol (67-56-1) + 5-(1-hydroxy-2-iodoethyl)uridine (123881-91-4,123881-92-5,144178-20-1) → 5-(1-methoxy-2-iodoethyl)uridine (123881-97-0,123881-98-1,144179-21-5)

Guidance literature:

With sulfuric acid; at 25 ℃; for 36h;

DOI:10.1021/jm00164a039

Reference yield:

5-iodouridine (1024-99-3) → 5-(1-methoxy-2-iodoethyl)uridine (123881-97-0,123881-98-1,144179-21-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / 1.) Et₃N, bis(triphenylphosphine)palladium(II) chloride / acetonitrile / 24 h / 80 °C

2: 99 percent / 0.5 N KOH / 2 h / 25 °C

3: 42 percent / triethylamine / dimethylformamide; H₂O / 20 h / 100 °C

4: 65 percent / I₂, KIO₃, 5 N H₂SO₄ / H₂O; acetonitrile / 0.5 h / 55 °C

5: 81 percent / 5 N H₂SO₄ / 36 h / 25 °C

With potassium iodate; potassium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; sulfuric acid; iodine; triethylamine; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00164a039

Reference yield:

(E)-5-(2-carboxyvinyl)uridine (99394-52-2) → 5-(1-methoxy-2-iodoethyl)uridine (123881-97-0,123881-98-1,144179-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / triethylamine / dimethylformamide; H₂O / 20 h / 100 °C

2: 65 percent / I₂, KIO₃, 5 N H₂SO₄ / H₂O; acetonitrile / 0.5 h / 55 °C

3: 81 percent / 5 N H₂SO₄ / 36 h / 25 °C

With potassium iodate; sulfuric acid; iodine; triethylamine; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00164a039

upstream raw materials:

methanol

5-(1-hydroxy-2-iodoethyl)uridine

5-iodouridine

(E)-5-(2-carboxyvinyl)uridine

Refernces