N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Base Information

• Chemical Name: N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine
• CAS No.: 865362-43-2
• Molecular Formula: C₄₄H₅₇N₅O₇SeSi
• Molecular Weight: 875.011

Synonyms:N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

There total 3 articles about N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine 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:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine (865362-41-0) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (865362-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

2.1: NaBH₄ / tetrahydrofuran; ethanol / 1 h / 20 °C

2.2: 49 percent / tetrahydrofuran / 0.33 h / 20 °C

With dmap; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja051694k

Reference yield:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (865362-40-9) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (865362-43-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / iPr₂NEt; CF₃COOK; 18-crown-6-ether / toluene / 11 h / 80 °C

2.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

3.1: NaBH₄ / tetrahydrofuran; ethanol / 1 h / 20 °C

3.2: 49 percent / tetrahydrofuran / 0.33 h / 20 °C

With dmap; sodium tetrahydroborate; 18-crown-6 ether; potassium trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ja051694k

Reference yield:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (415707-13-0) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylseleno-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (865362-43-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 60 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

2.1: 89 percent / iPr₂NEt; CF₃COOK; 18-crown-6-ether / toluene / 11 h / 80 °C

3.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

4.1: NaBH₄ / tetrahydrofuran; ethanol / 1 h / 20 °C

4.2: 49 percent / tetrahydrofuran / 0.33 h / 20 °C

With dmap; sodium tetrahydroborate; 18-crown-6 ether; potassium trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ja051694k

upstream raw materials:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Downstream raw materials:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoadenosine

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