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

Base Information

• Chemical Name: N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine
• CAS No.: 666724-46-5
• Molecular Formula: C₃₉H₄₉N₃O₇SeSi
• Molecular Weight: 778.879

Synonyms:N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine

Chemical Property of N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine

Chemical Property:

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Technology Process of N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine

There total 5 articles about N⁴-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine 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%

acetic anhydride (108-24-7) + 3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine (666724-45-4) → N4-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine (666724-46-5)

Guidance literature:

With pyridine; at 20 ℃; for 0.5h;

DOI:10.1021/ja038481k

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → N4-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine (666724-46-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 67 percent / pyridine / 20 °C

2: 92 percent / sodium borohydride / tetrahydrofuran; ethanol / 2 h / 20 °C

3: 95 percent / imidazole / dimethylformamide / 18 h / 20 °C

4: DMAP; triethylamine / CH₂Cl₂ / 1 h / 20 °C

5: 395 mg / aq. ammonia / tetrahydrofuran / 20 °C

6: 94 percent / pyridine / 0.5 h / 20 °C

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja038481k

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine (393802-82-9) → N4-acetyl-3'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methylcytidine (666724-46-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / imidazole / dimethylformamide / 18 h / 20 °C

2: DMAP; triethylamine / CH₂Cl₂ / 1 h / 20 °C

3: 395 mg / aq. ammonia / tetrahydrofuran / 20 °C

4: 94 percent / pyridine / 0.5 h / 20 °C

With pyridine; 1H-imidazole; dmap; ammonium hydroxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja038481k

upstream raw materials:

acetic anhydride

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

2,2'-Anhydrouridine

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine

Downstream raw materials:

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-methylseleno-2'-deoxycytidine

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