2-Amino-2'-O-methyladenosine

Base Information

• Chemical Name: 2-Amino-2'-O-methyladenosine
• CAS No.: 80791-87-3
• Molecular Formula: C₁₁H₁₆N₆O₄
• Molecular Weight: 296.286
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30432592
• Nikkaji Number: J1.173.370K
• Wikidata: Q72439059
• Mol file: 80791-87-3.mol

Synonyms:2-AMINO-2'-O-METHYLADENOSINE;80791-87-3;2'-O-METHYL-2,6-DIAMINOPURINE-RIBOSIDE;(2R,3R,4R,5R)-5-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol;(2R,3R,4R,5R)-5-(2,6-Diamino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol;2'-O-Methyl-2-aminoadenosine;MFCD01630959;SCHEMBL1527211;3'-O-Methyl-2-AMino-adenosine;DTXSID30432592;JLWUWXCKSOIFPS-KQYNXXCUSA-N;HG1391;AKOS015854658;CS-0137948;J-700023;J-700079;2,6-diamino-9-(2-O-methyl-beta-D-ribofuranosyl)purine;2,6-Diamino-9- (2'-O-methyl-beta-D-ribofuranosyl)purine;2,6-Diamino-9-(2' -O-methyl-beta-D-ribofuranosyl)purine;2,6-diamino-9-(2'-O-methyl-beta-D-ribofuranosyl) purine;2,6-Diamino-9-(2'-O-methyl-beta-D-ribofuranosyl)purine;(2R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol

Chemical Property of 2-Amino-2'-O-methyladenosine

Chemical Property:

• Melting Point: 121-122℃
• Boiling Point: 733.177 °C at 760 mmHg
• PKA: 13.12±0.70(Predicted)
• Flash Point: 397.211 °C
• PSA: 154.56000
• Density: 1.983 g/cm³
• LogP: -0.58130
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 296.12330301
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

98%Min ^*data from raw suppliers

2-Amino-2''-O-methyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1N2C=NC3=C(N=C(N=C32)N)N)CO)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=C(N=C32)N)N)CO)O
• Uses: 2-Amino-2''-O-methyladenosine is a derivative of 2-Aminoadenosine (A580360), which is a nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis.

Technology Process of 2-Amino-2'-O-methyladenosine

There total 4 articles about 2-Amino-2'-O-methyladenosine 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: 96.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + adenosine-2-amine (2096-10-8) → 2-amino-2'-O-methyladenosine (80791-87-3)

Guidance literature:

adenosine-2-amine; With tin(ll) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

diazomethane; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1080/15257770500544529

Reference yield: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + adenosine-2-amine (2096-10-8) → 2,6-diamino-9-(3-O-methyl-β-D-ribofuranosyl)purine (80791-88-4) + 2-amino-2'-O-methyladenosine (80791-87-3)

Guidance literature:

adenosine-2-amine; With tin(ll) chloride; In N,N-dimethyl-formamide; at 50 ℃; for 0.25h;

diazomethane; In N,N-dimethyl-formamide; at 50 ℃; Title compound not separated from byproducts;

DOI:10.1080/15257770500544529

Reference yield: 87.0%

→ 2-amino-2'-O-methyladenosine (80791-87-3)

Guidance literature:

upstream raw materials:

diazomethane

adenosine-2-amine

G

Downstream raw materials:

N²-isobutyryl-2′-O-methylguanosine

2'-O-methylguanosine

Refernces

• 1、 -. "2'-O-alkylnucleotides as well as polymers which contain such nucleotides". . . Retrieved 2008/06/13.
• 2、 -. "Novel adenosine derivatives and pharmaceutical composition containing them as an active ingredient". . . Retrieved 2008/06/13.