3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

Base Information

• Chemical Name: 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine
• CAS No.: 879015-11-9
• Molecular Formula: C₃₅H₅₁N₇O₆Si₂
• Molecular Weight: 722.004

Synonyms:3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

Chemical Property of 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

Chemical Property:

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Technology Process of 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

There total 5 articles about 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine 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: 94.0%

3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(adenin-9-yl)-methyl]-thymidine (879015-10-8) + benzoyl chloride (98-88-4) → 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N6-benzoyladenin-9-yl)-methyl]-thymidine (879015-11-9)

Guidance literature:

3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(adenin-9-yl)-methyl]-thymidine; benzoyl chloride; With pyridine; at 0 - 20 ℃;

With ammonia; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/jo052194c

Reference yield:

4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O2,5'-anhydrothymidine (879015-08-4) → 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N6-benzoyladenin-9-yl)-methyl]-thymidine (879015-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 46 percent / aq. NaOH / dioxane / 4 h / 20 °C

2.1: 58 percent / imidazole; pyridine / 20 °C

3.1: pyridine / 0 - 20 °C

3.2: 94 percent / NH₃ / methanol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; In 1,4-dioxane;

DOI:10.1021/jo052194c

Reference yield:

5'-O-[(trifluoromethyl)sulfonyl]-4'-C-[(trifluoromethylsulfonyl)-oxymethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-thymidine (879015-07-3) → 3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(N6-benzoyladenin-9-yl)-methyl]-thymidine (879015-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 64 percent / NaH; 18-crown-6 / dimethylformamide / 4 h / 50 °C

2.1: 46 percent / aq. NaOH / dioxane / 4 h / 20 °C

3.1: 58 percent / imidazole; pyridine / 20 °C

4.1: pyridine / 0 - 20 °C

4.2: 94 percent / NH₃ / methanol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; 18-crown-6 ether; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jo052194c

upstream raw materials:

3',5'-O-di[(1,1-dimethylethyl)dimethylsilyl]-4'-C-[(adenin-9-yl)-methyl]-thymidine

benzoyl chloride

4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-O²,5'-anhydrothymidine

4'-C-[(adenin-9-yl)methyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-thymidine

Downstream raw materials:

5'-O-(mono-4-methoxytrityl)-4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

4'-C-[(N⁶-benzoyladenin-9-yl)-methyl]-thymidine

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