N6-Methyl-2'-deoxyadenosine

Base Information

• Chemical Name: N6-Methyl-2'-deoxyadenosine
• CAS No.: 2002-35-9
• Molecular Formula: C11H15N5O3
• Molecular Weight: 265.272
• Hs Code.: 29349990
• UNII: 48QZW2IR9H
• DSSTox Substance ID: DTXSID60173840
• Nikkaji Number: J246.052A
• Wikidata: Q27107487
• Metabolomics Workbench ID: 68305
• ChEMBL ID: CHEMBL1875918
• Mol file: 2002-35-9.mol

Synonyms:2'-deoxy-N(6)-methyladenosine;N(6)-Me-dAdo;N(6)-methyl-2'-deoxyadenosine

Chemical Property of N6-Methyl-2'-deoxyadenosine

Chemical Property:

• Vapor Pressure: 2.03E-15mmHg at 25°C
• Refractive Index: 1.78
• Boiling Point: 603.6 °C at 760 mmHg
• PKA: 13.80±0.60(Predicted)
• Flash Point: 318.8 °C
• PSA: 105.32000
• Density: 1.72 g/cm³
• LogP: -0.41830
• Storage Temp.: −20°C
• Water Solubility.: Soluble in water
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 265.11748936
• Heavy Atom Count: 19
• Complexity: 321

Purity/Quality:

98%, ^*data from raw suppliers

2''-Deoxy-N-methyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C2C(=NC=N1)N(C=N2)C3CC(C(O3)CO)O
• Isomeric SMILES: CNC1=C2C(=NC=N1)N(C=N2)[C@H]3C[C@@H]([C@H](O3)CO)O
• Uses: 2''-Deoxy-N-methyladenosine plays role in catalytic activity and may promote proper folding of A730 loop.

Technology Process of N6-Methyl-2'-deoxyadenosine

There total 11 articles about N6-Methyl-2'-deoxyadenosine 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: 77.0%

N-1-methyl-2'-deoxyribofuranosiladenine iodide (74873-17-9) → N-6-methyl-2'-deoxyribofuranosil adenine (2002-35-9)

Guidance literature:

With sodium hydroxide; at 90 ℃;

DOI:10.1002/hlca.19860690511

Reference yield: 75.0%

(2R,3S,5R)-5-{6-[(Benzotriazol-1-ylmethyl)-amino]-purin-9-yl}-2-hydroxymethyl-tetrahydro-furan-3-ol → N-6-methyl-2'-deoxyribofuranosil adenine (2002-35-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 5h; Heating;

DOI:10.3891/acta.chem.scand.53-0280

Reference yield: 68.0%

2'-deoxy-1-methyladenosine hydroiodide → N-6-methyl-2'-deoxyribofuranosil adenine (2002-35-9)

Guidance literature:

In ammonium hydroxide; at 20 ℃; for 168h;

DOI:10.1002/hlca.200790093

upstream raw materials:

N-1-methyl-2'-deoxyribofuranosiladenine iodide

trimethylsulphonium hydroxide

2'-deoxy-D-adenosine

trimethylselenonium hydroxyde

Downstream raw materials:

2'-deoxy-D-adenosine

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester

<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine-3'-O-yl>(methoxy)morpholinophosphine

N-methyladenine

Refernces

• 1、 -. "Nucleoside analogue as well as preparation method and application thereof". Paragraph 0054; 0056; 0062; 0063; 0064; 0065. . Retrieved 2021/05/12.
• 2、 El-Kafrawy, Sherif A.,Zahran, Magdy A.,Pedersen, Erik B.. "A Novel Route to N6-Alkylated 2′-Deoxyadenosine Using Benzotriazole as a Synthetic Auxiliary". . p. 280 - 283. Retrieved 2007/10/03.