O(6)-Methyl-2'-deoxyguanosine

Base Information

• Chemical Name: O(6)-Methyl-2'-deoxyguanosine
• CAS No.: 964-21-6
• Molecular Formula: C11H15 N5 O4
• Molecular Weight: 281.271
• DSSTox Substance ID: DTXSID60242222
• Nikkaji Number: J366.857F
• Wikidata: Q27103189
• Metabolomics Workbench ID: 51368
• Mol file: 964-21-6.mol

Synonyms:2'-deoxy-O(6)-methylguanosine;O(6)-methyl-2'-deoxyguanosine;O(6)-methyl-2'-deoxyguanosine, (alpha)-isomer;O(6)-methyldeoxyguanosine

Chemical Property of O(6)-Methyl-2'-deoxyguanosine

Chemical Property:

• Boiling Point: 674.7 °C at 760 mmHg
• Flash Point: 361.9 °C
• PSA: 128.54000
• Density: 1.84 g/cm³
• LogP: -0.36100
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

99%, ^*data from raw suppliers

O6-Methyl-2’-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=NC2=C1N=CN2C3CC(C(O3)CO)O)N
• Isomeric SMILES: COC1=NC(=NC2=C1N=CN2[C@H]3C[C@@H]([C@H](O3)CO)O)N
• Uses: O6-Methyl-2’-deoxyguanosine is a ubiquitous DNA lesion formed by xenobiotic carcinogens and endogenous methylating agent, S-adenosyl-L-methionine. A mutagenic adducts formed by a potent tobacco carcinogen, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).

Technology Process of O(6)-Methyl-2'-deoxyguanosine

There total 36 articles about O(6)-Methyl-2'-deoxyguanosine 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: 100.0%

2'-deoxy-N2-isobutyryl-O6-methylguanosine (82921-45-7) → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine (964-21-6,52225-08-8)

Guidance literature:

With ammonium hydroxide; at 50 ℃; for 72h;

DOI:10.1016/S0040-4039(00)87314-1

Reference yield: 85.0%

2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine (128790-76-1) + sodium methylate (124-41-4) → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine (964-21-6,52225-08-8)

Guidance literature:

In methanol; at 55 ℃; for 36h;

DOI:10.1021/jo00051a051

Reference yield: 76.0%

2-amino-9-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythto-pentofuranosyl]-6-methoxy-9-H-purine → 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine (964-21-6,52225-08-8)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1002/hlca.19960790215

upstream raw materials:

2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine

sodium methylate

2'-Deoxyguanosine

trimethylsulphonium hydroxide

Downstream raw materials:

N-benzoyl-5'-dimethoxytrityl-O⁶-methyldeoxyguanosine

N²-benzoyl-O⁶-methyldeoxyguanosine

N²,O³,O⁵-tribenzoyl-O⁶-methyldeoxyguanosine

Refernces

• 1、 -. "NUCLEOTIDE PRODRUGS". . . Retrieved 2019/07/20.
• 2、 Janeba, Zlatko,Lin, Xiaoyu,Robins, Morris J.. "Functionalization of Guanosine and 2′-Deoxyguanosine at C6: A Modified Appel Process and SNAr Displacement of Imidazole". . p. 137 - 147. Retrieved 2007/10/03.