N7-Methylguanosine

Base Information

• Chemical Name: N7-Methylguanosine
• CAS No.: 22164-16-5
• Deprecated CAS: 34080-10-9
• Molecular Formula: C11H15 N5 O5
• Molecular Weight: 297.271
• UNII: 5290OM2I6G
• DSSTox Substance ID: DTXSID20328798
• Nikkaji Number: J1.744.817J
• Wikipedia: 7-Methylguanosine
• Wikidata: Q27260988
• Metabolomics Workbench ID: 67126
• ChEMBL ID: CHEMBL4096809
• Mol file: 22164-16-5.mol

Synonyms:2-methylguanosine;7-methylguanosine;N(2)-methylguanosine

Chemical Property of N7-Methylguanosine

Chemical Property:

• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 297.10731860
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=[N+](C2=C1C(=NC(=N2)N)[O-])C3C(C(C(O3)CO)O)O
• Isomeric SMILES: CN1C=[N+](C2=C1C(=NC(=N2)N)[O-])[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O

Technology Process of N7-Methylguanosine

There total 2 articles about N7-Methylguanosine 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: 54.0%

trimethylsulphonium iodide (2181-42-2) + G (118-00-3) → 7-methylguanine (578-76-7) + 7-methylguanosine (22164-16-5) + 2-amino-5-(formylmethylamino)-4-(1-furanosylamino)pyrimidine-6(1H)-one (39708-05-9)

Guidance literature:

In N,N-dimethyl-formamide; at 85 ℃; for 3.5h;

Reference yield: 7.0%

1-methyl-1-nitrosourea (684-93-5) + G (118-00-3) → 2'-O-methylguanosine (2140-71-8) + 7-methylguanosine (22164-16-5) + N2-Methylguanosine (2140-77-4) + 1-methylguanosine (2140-65-0)

Guidance literature:

With borax; In water; formamide; at 50 ℃; for 18h;

DOI:10.1002/anie.201801919

Reference yield: 81.0%

C12H11N(15)N4O + 7-methylguanosine (22164-16-5) → 6‐((4‐hydroxybenzyl)amino)‐[15N4]purine‐9‐β‐D-ribofuranoside

Guidance literature:

C₁₂H₁₁N⁽¹⁵⁾N₄O; 7-methylguanosine; With dipotassium hydrogenphosphate; In ethanol; water; at 70 ℃;

With purine nucleotide phosphorylase; In ethanol; water; at 35 ℃; for 168h; Sealed tube; Enzymatic reaction;

DOI:10.1002/jlcr.3702

upstream raw materials:

trimethylsulphonium iodide

G

1-methyl-1-nitrosourea

Downstream raw materials:

7-methylguanine

ribavirin

3-deazaadenosine

7-methylguanine

Refernces

• 1、 Yamauchi, Kiyoshi,Nakagima, Toru,Kinoshita, Masayoshi. "Methylation study of ribonucleosides, deoxyribonucleosides, and 2′-O-methylribonucleosides with trimethylsulphonium hydroxide and trimethylsulphonium iodide. Influence of the 2′-hydroxy-groups on the reactivity of the base moieties of ribonucleosides". . p. 2787 - 2792. Retrieved 2007/10/02.