2-Amino-3'-O-(2-methoxyethyl)adenosine

Base Information

• Chemical Name: 2-Amino-3'-O-(2-methoxyethyl)adenosine
• CAS No.: 256224-02-9
• Molecular Formula: C₁₃H₂₀N₆O₅
• Molecular Weight: 340.339
• DSSTox Substance ID: DTXSID10595816
• Wikidata: Q82490910
• Mol file: 256224-02-9.mol

Synonyms:256224-02-9;(2R,3R,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-ol;2-Amino-3/'-O-(2-methoxyethyl)adenosine;2-AMINO-3'-O-(2-METHOXYETHYL)ADENOSINE;(2R,3R,4S,5R)-2-(2,6-Diamino-9H-purin-9-yl)-5-(hydroxymethyl)-4-(2-methoxyethoxy)tetrahydrofuran-3-ol;SCHEMBL3624213;DTXSID10595816;(2R,3R,4S,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-ol;AKOS015967466

Chemical Property of 2-Amino-3'-O-(2-methoxyethyl)adenosine

Chemical Property:

• Boiling Point: 734.5±70.0 °C(Predicted)
• PKA: 12.95±0.70(Predicted)
• PSA: 163.79000
• Density: 1.81±0.1 g/cm3(Predicted)
• LogP: -0.56470
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 340.14951776
• Heavy Atom Count: 24
• Complexity: 420

Purity/Quality:

97% ^*data from raw suppliers

2-AMINO-3'-O-(2-METHOXYETHYL)ADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCOC1C(OC(C1O)N2C=NC3=C(N=C(N=C32)N)N)CO
• Isomeric SMILES: COCCO[C@@H]1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C(N=C(N=C32)N)N)CO

Technology Process of 2-Amino-3'-O-(2-methoxyethyl)adenosine

There total 12 articles about 2-Amino-3'-O-(2-methoxyethyl)adenosine 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: 47.0%

2-methoxyethyl methanesulfonate (16427-44-4) + adenosine-2-amine (2096-10-8) → 3'-O-methoxyethyl-2,6-diaminopurine riboside (256224-02-9) + C16H26N6O6 (847647-19-2) + 2'-O-(2-methoxyethyl)-2,6-diaminopurine riboside (256224-13-2)

Guidance literature:

2-methoxyethyl methanesulfonate; adenosine-2-amine; With sodium hydride; lithium bromide; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 50 - 52 ℃; for 3h;

2-methoxyethyl methanesulfonate; With potassium hydroxide; In dimethyl sulfoxide; for 18h; Further stages.;

DOI:10.1080/15257770701528180

Reference yield: 45.0%

2-Bromoethyl methyl ether (6482-24-2) + adenosine-2-amine (2096-10-8) → 3'-O-methoxyethyl-2,6-diaminopurine riboside (256224-02-9) + C16H26N6O6 (847647-19-2) + C19H32N6O7 + 2'-O-(2-methoxyethyl)-2,6-diaminopurine riboside (256224-13-2)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 6h;

DOI:10.1080/15257770802271748

Reference yield:

C27H28N6O7 → 3'-O-methoxyethyl-2,6-diaminopurine riboside (256224-02-9)

Guidance literature:

With ammonium hydroxide; In methanol; at 25 ℃;

upstream raw materials:

2-methoxyethyl methanesulfonate

adenosine-2-amine

2-Bromoethyl methyl ether

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

Refernces

• 1、 -. "A 3' - oxygen - methoxy ethyl nucleoside preparation method (by machine translation)". . . Retrieved 2018/09/11.
• 2、 Sivets, Grigorii G.. "Synthesis study of 2′-O-(2-methoxyethyl)-purine derivatives". . p. 1237 - 1240. Retrieved 2008/09/18.