2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

Base Information

• Chemical Name: 2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine
• CAS No.: 596112-06-0
• Molecular Formula: C₁₇H₁₉N₃O₅
• Molecular Weight: 345.355
• Mol file: 596112-06-0.mol

Synonyms:2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

Chemical Property of 2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

There total 10 articles about 2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine 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: 100.0%

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-05-9) → 2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-06-0)

Guidance literature:

With triethylamine trihydrofluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/jo034263y

Reference yield:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9) → 2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-06-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / ammonia gas / methanol / 48 h / 0 - 4 °C

2: 65 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: DMAP / acetonitrile / 1 h / 20 °C

4: 0.502 g / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / Heating

5: triethylamine; DMAP / acetonitrile / 53 h / 20 °C

6: 0.337 g / ammonium hydroxide / H₂O; acetonitrile / 3 h / 20 °C

7: 93 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

8: 100 percent / triethylamine trihydrofluoride / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; dmap; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); triethylamine trihydrofluoride; ammonia; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo034263y

Reference yield:

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methyluridine → 2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; DMAP / acetonitrile / 53 h / 20 °C

2: 0.337 g / ammonium hydroxide / H₂O; acetonitrile / 3 h / 20 °C

3: 93 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 100 percent / triethylamine trihydrofluoride / tetrahydrofuran / 4 h / 20 °C

With dmap; ammonium hydroxide; triethylamine trihydrofluoride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/jo034263y

upstream raw materials:

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

2'-C-methyluridine

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-C-β-methyluridine

Downstream raw materials:

5'-O-(dimethoxytrityl)-2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine

Refernces

• 1、 Li, Nan-Sheng,Piccirilli, Joseph A.. "Synthesis of the phosphoramidite derivative of 2′-deoxy-2′-C-β-methylcytidine". . p. 6799 - 6802. Retrieved 2007/10/03.