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

Base Information

• Chemical Name: 1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 151384-13-3
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.232
• Mol file: 151384-13-3.mol

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

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

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 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:

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine (23643-36-9) → 1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (151384-13-3)

Guidance literature:

Multi-step reaction with 5 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: TBAF / tetrahydrofuran / 1 h / 20 °C

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

DOI:10.1021/jo034263y

Reference yield:

1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (151384-13-3) → 2'-deoxy-2'-α-methyl-N4-benzoylcytidine (733050-27-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / imidazole / dimethylformamide / 20 - 60 °C

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

2.2: 87 percent / NH₄OH / acetonitrile / 3 h / 20 °C

3.1: 97 percent / DMAP / CH₂Cl₂ / 20 °C

4.1: 75 percent / triethylamine trihydrofluoride; Et₃N / tetrahydrofuran / 20 - 60 °C

With 1H-imidazole; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine trihydrofluoride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0495337

Reference yield:

1-((2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (151384-13-3) → 3',5'-di-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-α-methyl-N4-benzoylcytidine (733050-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / imidazole / dimethylformamide / 20 - 60 °C

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

2.2: 87 percent / NH₄OH / acetonitrile / 3 h / 20 °C

3.1: 97 percent / DMAP / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0495337

upstream raw materials:

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

Downstream raw materials:

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

3',5'-di-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

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