5-Iodo-2'-O-methyluridine

Base Information

• Chemical Name: 5-Iodo-2'-O-methyluridine
• CAS No.: 34218-84-3
• Molecular Formula: C10H13 I N2 O6
• Molecular Weight: 384.128
• DSSTox Substance ID: DTXSID501312637
• Mol file: 34218-84-3.mol

Synonyms:5-Iodo-2'-O-methyluridine;34218-84-3;1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-iodopyrimidine-2,4-dione;SCHEMBL15367277;PLVDDNNLEWFJNQ-JXOAFFINSA-N;DTXSID501312637;2-(O-METHYL)-5-IODOURIDINE;MFCD04973692;AKOS024463672;AC-32310;F12934;A848742;1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 5-Iodo-2'-O-methyluridine

Chemical Property:

• PKA: 7.94±0.10(Predicted)
• PSA: 113.78000
• Density: 2.04±0.1 g/cm3(Predicted)
• LogP: -1.59320
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 383.98183
• Heavy Atom Count: 19
• Complexity: 428

Purity/Quality:

97% ^*data from raw suppliers

5-Iodo-2’-O-methyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1N2C=C(C(=O)NC2=O)I)CO)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)I)CO)O
• Uses: 5-Iodo-2’-O-methyluridine is a nucleoside analog (NSA) which acts as a chemotherapeutic agent for the induction of neuronal differentiation.

Technology Process of 5-Iodo-2'-O-methyluridine

There total 2 articles about 5-Iodo-2'-O-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: 92.4%

2'-O-methyluridine (2140-76-3) → 1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione (34218-84-3)

Guidance literature:

With ammonium cerium(IV) nitrate; iodine; In acetonitrile; at 80 ℃; for 2.5h;

Reference yield:

→ 1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione (34218-84-3)

Guidance literature:

DOI:10.1021/bi00795a017

Reference yield: 84.5%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione (34218-84-3) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-5-iodouridine

Guidance literature:

With pyridine; at 20 ℃; Cooling with ice;

upstream raw materials:

2'-O-methyluridine

Downstream raw materials:

Acetic acid 2-acetoxy-1-(1-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-ethyl ester

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