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

Base Information

• Chemical Name: 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine
• CAS No.: 160054-76-2
• Molecular Formula: C₃₈H₃₇N₃O₇
• Molecular Weight: 647.728
• Mol file: 160054-76-2.mol

Synonyms:5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

Chemical Property of 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

There total 17 articles about 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-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: 80.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-2'-α-methyl-N4-benzoylcytidine (733050-27-6) → 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N4-benzoylcytidine (160054-76-2)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1021/jo0495337

Reference yield:

methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside (733050-11-8) → 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N4-benzoylcytidine (160054-76-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

1.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

2.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

3.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

4.1: TMS₂NH; (NH₄)2SO₄ / Heating

4.2: SnCl₄ / acetonitrile / 20 °C

5.1: 98 percent / aq. NaOH / methanol / 1 h / 20 °C

6.1: DMAP; phenyl chlorothionoformate / acetonitrile / 5 h / 20 °C

7.1: 59 mg / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

8.1: 147 mg / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 24 h / 20 °C

9.1: 80 percent / imidazole / dimethylformamide / 20 - 60 °C

10.1: Et₃N; 2,4,6-triisopropylbenzenesulfonyl chloride; DMAP / acetonitrile / 24 h / 20 °C

10.2: 87 percent / NH₄OH / acetonitrile / 3 h / 20 °C

11.1: 97 percent / DMAP / CH₂Cl₂ / 20 °C

12.1: 75 percent / triethylamine trihydrofluoride; Et₃N / tetrahydrofuran / 20 - 60 °C

13.1: 80 percent / pyridine; DMAP / 20 °C

With pyridine; 1H-imidazole; dmap; ammonium sulfate; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-triisopropylphenylsulfonyl chloride; 2,2'-azobis(isobutyronitrile); triethylamine trihydrofluoride; hydrogen; sec.-butyllithium; tri-n-butyl-tin hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; phenylcarbonochloridothioate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo0495337

Reference yield:

methyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-methylene-β-D-ribofuranoside (733050-12-9) → 5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N4-benzoylcytidine (160054-76-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

1.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

2.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: TMS₂NH; (NH₄)2SO₄ / Heating

3.2: SnCl₄ / acetonitrile / 20 °C

4.1: 98 percent / aq. NaOH / methanol / 1 h / 20 °C

5.1: DMAP; phenyl chlorothionoformate / acetonitrile / 5 h / 20 °C

6.1: 59 mg / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

7.1: 147 mg / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 24 h / 20 °C

8.1: 80 percent / imidazole / dimethylformamide / 20 - 60 °C

9.1: Et₃N; 2,4,6-triisopropylbenzenesulfonyl chloride; DMAP / acetonitrile / 24 h / 20 °C

9.2: 87 percent / NH₄OH / acetonitrile / 3 h / 20 °C

10.1: 97 percent / DMAP / CH₂Cl₂ / 20 °C

11.1: 75 percent / triethylamine trihydrofluoride; Et₃N / tetrahydrofuran / 20 - 60 °C

12.1: 80 percent / pyridine; DMAP / 20 °C

With pyridine; 1H-imidazole; dmap; ammonium sulfate; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-triisopropylphenylsulfonyl chloride; 2,2'-azobis(isobutyronitrile); triethylamine trihydrofluoride; hydrogen; tri-n-butyl-tin hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; phenylcarbonochloridothioate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo0495337

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside

1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione