6-O-Methyl Guanosine

Base Information

• Chemical Name: 6-O-Methyl Guanosine
• CAS No.: 7803-88-5
• Molecular Formula: C11H15N5O5
• Molecular Weight: 297.271
• DSSTox Substance ID: DTXSID10861265
• Nikkaji Number: J533.517E
• Wikidata: Q15632797
• ChEMBL ID: CHEMBL406852
• Mol file: 7803-88-5.mol

Synonyms:6'-O-methylguanosine;O(6)-methylguanosine;O6-methylguanosine

Chemical Property of 6-O-Methyl Guanosine

Chemical Property:

• Vapor Pressure: 8.06E-22mmHg at 25°C
• Melting Point: 120 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• Refractive Index: 1.829
• Boiling Point: 721 °C at 760 mmHg
• PKA: 13.07±0.70(Predicted)
• Flash Point: 389.9 °C
• PSA: 148.77000
• Density: 1.98 g/cm³
• LogP: -1.39020
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Very Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 297.10731860
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

95%min ^*data from raw suppliers

O6-Methylguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: COC1=NC(=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• Uses: A guanine derivative that acts as modulators of GTPases and modulator-resistant enzymes; used in drug design and target validation. 6-O-Methyl Guanosine is a guanine derivative that acts as modulators of GTPases and modulator-resistant enzymes; used in drug design and target validation

Technology Process of 6-O-Methyl Guanosine

There total 6 articles about 6-O-Methyl Guanosine 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: 53.0%

trimethylsulphonium hydroxide (17287-03-5) + G (118-00-3) → 1,2'-Dimethylguanosine (73667-71-7) + 1,3'-Dimethylguanosine (74466-66-3) + 1-methylguanosine (2140-65-0) + 6-O-methylguanosine (7803-88-5)

Guidance literature:

In methanol; N,N-dimethyl-formamide; at 70 ℃; for 1h; Further byproducts given;

Reference yield: 5.0%

trimethylphenylammonium hydroxide (1899-02-1) + G (118-00-3) → 1,2'-Dimethylguanosine (73667-71-7) + 1,3'-Dimethylguanosine (74466-66-3) + 1-methylguanosine (2140-65-0) + 6-O-methylguanosine (7803-88-5)

Guidance literature:

In N,N-dimethyl-formamide; at 100 ℃;

Reference yield:

methanol (67-56-1) + 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine (3387-63-1) → 2-Amino-6-chloropurine riboside (2004-07-1) + 6-O-methylguanosine (7803-88-5) + adenosine-2-amine (2096-10-8)

Guidance literature:

With ammonia; at 50 ℃; for 16h;

DOI:10.1021/jo061885l

upstream raw materials:

trimethylsulphonium hydroxide

G

trimethylphenylammonium hydroxide

methanol

Downstream raw materials:

(2R,3R,4R,5R)-5-(2-acetamido-6-methoxy-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl but-3-yn-1-yl diisopropylphosphoramidite

2-Acetonyl-9-(3'-deoxy-β-D-ribofuranosyl)hypoxanthine

O⁶,7-dimethylguanine

Refernces

• 1、 Bookser, Brett C.,Raffaele, Nicholas B.. "High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries". . p. 173 - 179. Retrieved 2007/10/03.
• 2、 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.