3'-C-Methyladenosine

Base Information

• Chemical Name: 3'-C-Methyladenosine
• CAS No.: 15397-13-4
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.271
• Nikkaji Number: J1.719.377E
• ChEMBL ID: CHEMBL480143
• Mol file: 15397-13-4.mol

Synonyms:3'-C-methyladenosine;3'-Me-Ado

Chemical Property of 3'-C-Methyladenosine

Chemical Property:

• Boiling Point: 643.4±65.0 °C(Predicted)
• Density: 1.89±0.1 g/cm3(Predicted)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(OC(C1O)N2C=NC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: C[C@]1([C@H](O[C@H]([C@@H]1O)N2C=NC3=C(N=CN=C32)N)CO)O

Technology Process of 3'-C-Methyladenosine

There total 19 articles about 3'-C-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: 72.0%

9-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)-N6-benzoyladenine (115236-92-5) → 3'-methyl-adenosine (15397-13-4,70723-11-4,115236-97-0)

Guidance literature:

With ammonium hydroxide; at 20 ℃; for 48h;

DOI:10.1016/0008-6215(88)84024-2

Reference yield:

5'-O-(p-methoxyphenyldiphenylmethyl)adenosine (51600-11-4) → 9-(3'-C-methyl-β-D-xylo-furanosyl)adenine (15397-13-4,70723-11-4,115236-97-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / AgNO₃, pyridine / tetrahydrofuran / 8 h

2: 55 percent / CrO₃, pyridine, AcO₂ / CH₂Cl₂ / 0.75 h / 20 °C

3: 60 percent / diethyl ether; tetrahydrofuran / 1 h

4: tetrabutylammonium fluoride / tetrahydrofuran / 30 h / 20 °C

5: aq. AcOH / dioxane / 2 h

With pyridine; chromium(VI) oxide; AcO₂; tetrabutyl ammonium fluoride; silver nitrate; acetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;

Reference yield:

adenosine (58-61-7) → 9-(3'-C-methyl-β-D-xylo-furanosyl)adenine (15397-13-4,70723-11-4,115236-97-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / pyridine / Ambient temperature

2: 60 percent / AgNO₃, pyridine / tetrahydrofuran / 8 h

3: 55 percent / CrO₃, pyridine, AcO₂ / CH₂Cl₂ / 0.75 h / 20 °C

4: 60 percent / diethyl ether; tetrahydrofuran / 1 h

5: tetrabutylammonium fluoride / tetrahydrofuran / 30 h / 20 °C

6: aq. AcOH / dioxane / 2 h

With pyridine; chromium(VI) oxide; AcO₂; tetrabutyl ammonium fluoride; silver nitrate; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane;

upstream raw materials:

9-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)-N⁶-benzoyladenine

5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine

3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine

5'-O-(p-methoxyphenyldiphenylmethyl)adenosine