5-Methoxymethyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-Methoxymethyl-2'-deoxyuridine
• CAS No.: 5116-22-3
• Molecular Formula: C11H16 N2 O6
• Molecular Weight: 272.258
• DSSTox Substance ID: DTXSID00199185
• Nikkaji Number: J93.352J
• Wikidata: Q76010089
• Mol file: 5116-22-3.mol

Synonyms:2'-deoxy-5-methoxymethyluridine;5-methoxymethyl-2'-deoxyuridine;5-methoxymethyldeoxyuridine;MMUdR

Chemical Property of 5-Methoxymethyl-2'-deoxyuridine

Chemical Property:

• PSA: 113.78000
• Density: 1.427g/cm3
• LogP: -1.67630
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 272.10083623
• Heavy Atom Count: 19
• Complexity: 410

Purity/Quality:

97% ^*data from raw suppliers

5-Methoxymethyl-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: COCC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
• Uses: 5-Methoxymethyl-2''-deoxyuridine can be used in biological study of synthesis and in vitro antimycobacterial activity of substituted pyrimidine nucleosides.

Technology Process of 5-Methoxymethyl-2'-deoxyuridine

There total 10 articles about 5-Methoxymethyl-2'-deoxyuridine 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: 78.0%

3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(methyl)oxymethyluridine (629642-50-8) → 2'-deoxy-5-(methoxymethyl)uridine (5116-22-3)

Guidance literature:

With pyridine; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/anie.200604635

Reference yield:

→ 5-Methoxymethyl-desoxy-uridin (5116-22-3,30652-57-4,104639-39-6)

Guidance literature:

S.236;

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 2'-deoxy-5-(methoxymethyl)uridine (5116-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide; azoisobutyronitrile / benzene / 0.67 h / 80 °C

2: 61 percent / NaOMe / 2 h

3: 78 percent / Et₃N*3HF; pyridine / tetrahydrofuran / 16 h / 20 °C

With pyridine; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium methylate; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; benzene;

DOI:10.1002/anie.200604635

upstream raw materials:

sodium methylate

3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine

3',5'-di-O-acetyl-5-(methoxymethyl)-2'-deoxyuridine

3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(methyl)oxymethyluridine

Downstream raw materials:

5-methoxymethyl-5'-triphenylmethyl-2'-deoxyuridine

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methoxymethyluridine

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methoxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

(1R,9R,10R)-4-Methoxymethyl-10-trityloxymethyl-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one