2',3'-DIMETHOXYADENOSINE

Base Information

• Chemical Name: 2',3'-DIMETHOXYADENOSINE
• CAS No.: 20649-46-1
• Molecular Formula: C₁₂H₁₇N₅O₄
• Molecular Weight: 295.298
• Mol file: 20649-46-1.mol

Synonyms:2',3'-O-Dimethyladenosine;2',3'-Di-O-Methyladenosin;O2',O3'-dimethyl-adenosine;2'-O,3'-O-dimethyladenosine;O2',O3'-Dimethyladenosin;

Chemical Property of 2',3'-DIMETHOXYADENOSINE

Chemical Property:

• Melting Point: 167-172°C
• PSA: 117.54000
• LogP: -0.09060
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

2’,3’-Di-O-methyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2’,3’-Di-O-methyladenosine is a derivative of 2-Amino Adenosine (A580360), which is a nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis.

Technology Process of 2',3'-DIMETHOXYADENOSINE

There total 9 articles about 2',3'-DIMETHOXYADENOSINE 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: 28.0%

trimethylsulphonium hydroxide (17287-03-5) + adenosine (58-61-7) → N6,O2'-methyladenosine (57817-83-1) + 2'-O,3'-O-dimethyladenosine (20649-46-1) + 2'-O-methyl adenosine (2140-79-6) + 3'-O-methyladenosine (10300-22-8)

Guidance literature:

With bis(acetylacetonate)nickel(II); In N,N-dimethyl-formamide; at 70 ℃; for 1h; Further byproducts given;

DOI:10.1021/jo01307a026

Reference yield: 18.0%

2'-O-methyl adenosine (2140-79-6) + trimethylselenonium hydroxyde (74230-06-1) → N6,O2'-methyladenosine (57817-83-1) + 2'-O,3'-O-dimethyladenosine (20649-46-1)

Guidance literature:

With copper acetylacetonate; In N,N-dimethyl-formamide; at 70 ℃; for 0.5h; Product distribution; reaction without copper(II) acetylacetonate;

Reference yield: 17.0%

trimethylselenonium hydroxyde (74230-06-1) + 3'-O-methyladenosine (10300-22-8) → N6,O3'-methyladenosine (60037-52-7) + 2'-O,3'-O-dimethyladenosine (20649-46-1)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 0.5h; Product distribution; reaction with copper(II) acetylacetonate;

upstream raw materials:

trimethylsulphonium hydroxide

2'-O-methyl adenosine

trimethylselenonium hydroxyde

adenosine

Refernces

• 1、 -. "ADENOSINE DEAMINASE INHIBITOR". . . Retrieved 2008/06/13.
• 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.