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

Base Information

• Chemical Name: 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N⁴-benzoylcytidine
• CAS No.: 596112-05-9
• Molecular Formula: C₂₉H₄₅N₃O₆Si₂
• Molecular Weight: 587.864
• Mol file: 596112-05-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-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: 93.0%

benzoyl chloride (98-88-4) + 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methylcytidine → 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-05-9) + 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-α-methyl-N4-benzoylcytidine

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo034263y

Reference yield:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9) → 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-05-9)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/jo034263y

Reference yield:

benzoyl chloride (98-88-4) + (2'S)-3'5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-methylcytidine (596112-04-8) → 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-05-9)

Guidance literature:

With pyridine; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.02.047

upstream raw materials:

benzoyl chloride

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

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