2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one

Base Information

• Chemical Name: 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one
• CAS No.: 10300-27-3
• Molecular Formula: C11H15 N5 O5
• Molecular Weight: 297.2673
• Mol file: 10300-27-3.mol

Synonyms:3'-O-Methylguanosine;NSC 106541

Chemical Property of 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one

Chemical Property:

• Melting Point: 263-300 °C (decomp)
• Boiling Point: 711.7°Cat760mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 384.2°C
• PSA: 148.51000
• Density: 1.98g/cm³
• LogP: -1.45140

Purity/Quality:

99.3% ^*data from raw suppliers

3''-O-Methylguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one

There total 5 articles about 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one 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: 18.0%

trimethylsulphonium hydroxide (17287-03-5) + G (118-00-3) → 3’-O-methylguanosine (10300-27-3) + 2'-O-methylguanosine (2140-71-8) + 1,2'-Dimethylguanosine (73667-71-7) + 1-methylguanosine (2140-65-0)

Guidance literature:

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

Reference yield: 18.0%

trimethylsulphonium hydroxide (17287-03-5) + G (118-00-3) → 3’-O-methylguanosine (10300-27-3) + 2'-O-methylguanosine (2140-71-8) + 1,3'-Dimethylguanosine (74466-66-3) + 1-methylguanosine (2140-65-0)

Guidance literature:

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

DOI:10.1021/jo01307a026

Reference yield:

9-[(2R,3R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-1,9-dihydro-purin-6-one (125132-18-5) → 3’-O-methylguanosine (10300-27-3) + 2-amino-9-((2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purine-6-one (123402-21-1)

Guidance literature:

With pyridine; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, r.t., 2.) CH₂Cl₂;

DOI:10.1039/c39890000955

upstream raw materials:

trimethylsulphonium hydroxide

G

9-[(2R,3R,4S,5R)-4-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-1,9-dihydro-purin-6-one

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.