N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• CAS No.: 1608109-26-7
• Molecular Formula: C₄₂H₄₉F₃N₅O₈PS
• Molecular Weight: 871.915

Synonyms:N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Chemical Property of N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Chemical Property:

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Technology Process of N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

There total 5 articles about N⁴-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 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%

N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine (1608109-25-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → N4-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (1608109-26-7)

Guidance literature:

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine; With N,N-dimethyl-ethanamine; In dichloromethane; at 20 ℃; for 0.416667h; Inert atmosphere;

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine; In dichloromethane; for 2.5h; Inert atmosphere;

DOI:10.1021/ja5005637

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-21-2) → N4-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (1608109-26-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: ammonia / tetrahydrofuran; water / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: N,N-dimethyl-ethanamine / dichloromethane / 0.42 h / 20 °C / Inert atmosphere

5.2: 2.5 h / Inert atmosphere

With pyridine; dmap; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; ammonia; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja5005637

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-22-3) → N4-acetyl-5‘-O-(4,4‘-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (1608109-26-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonia / tetrahydrofuran; water / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: N,N-dimethyl-ethanamine / dichloromethane / 0.42 h / 20 °C / Inert atmosphere

4.2: 2.5 h / Inert atmosphere

With pyridine; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; ammonia; acetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja5005637

upstream raw materials:

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiouridine

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine

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