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

Base Information

• Chemical Name: 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine
• CAS No.: 1608109-22-3
• Molecular Formula: C₅₂H₆₅F₃N₂O₉S₂Si
• Molecular Weight: 1011.31

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

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

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

There total 3 articles about 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine 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: 66.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-21-2) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-22-3)

Guidance literature:

2,4,6-triisopropylphenylsulfonyl chloride; 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiouridine; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

Inert atmosphere;

DOI:10.1021/ja5005637

Reference yield:

C31H29F3N2O7S (1421694-67-8) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

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

2.2: Inert atmosphere

With 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja5005637

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-O6-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxy-2'-trifluoromethylthiouridine (1608109-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

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

2.2: Inert atmosphere

With 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja5005637

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

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

C₃₁H₂₉F₃N₂O₇S

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

N⁴-acetyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-trifluoromethylthiocytidine

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

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

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