N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine

Base Information

• Chemical Name: N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine
• CAS No.: 340721-57-5
• Molecular Formula: C₅₁H₆₅N₅O₇Si₂
• Molecular Weight: 916.277

Synonyms:N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine

Chemical Property of N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine

There total 5 articles about N⁶-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)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: 89.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N6-benzoyl-2'-deoxy-8-(hydroxymethyl)-3',5'-bis-O-(triethylsilyl)adenosine (340721-56-4) → N6-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine (340721-57-5)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 23 ℃; for 16h;

DOI:10.1002/1522-2675(20010321)84:3<594::AID-HLCA594>3.0.CO;2-9

Reference yield:

triethylsilyl chloride (994-30-9) → N6-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine (340721-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / imidazole / dimethylformamide / 16 h / 23 °C

2.1: LDA / tetrahydrofuran; hexane / 2.5 h / -70 °C

3.1: AcOH / tetrahydrofuran / 23 °C

3.2: NaBH₄ / ethanol; tetrahydrofuran; acetic acid / 0.42 h / 23 °C

4.1: 89 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 16 h / 23 °C

With 1H-imidazole; dmap; acetic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20010321)84:3<594::AID-HLCA594>3.0.CO;2-9

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → N6-benzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]-3',5'-bis-O-(triethylsilyl)adenosine (340721-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / imidazole / dimethylformamide / 16 h / 23 °C

2.1: LDA / tetrahydrofuran; hexane / 2.5 h / -70 °C

3.1: AcOH / tetrahydrofuran / 23 °C

3.2: NaBH₄ / ethanol; tetrahydrofuran; acetic acid / 0.42 h / 23 °C

4.1: 89 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 16 h / 23 °C

With 1H-imidazole; dmap; acetic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20010321)84:3<594::AID-HLCA594>3.0.CO;2-9

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁶-benzoyl-2'-deoxy-8-(hydroxymethyl)-3',5'-bis-O-(triethylsilyl)adenosine

triethylsilyl chloride

N₆-benzoyl-2'-deoxyadenosine

Downstream raw materials:

N⁶,5-dibenzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]adenosine 3'-(2-cyanoethyl diisopropylphosphoramidite)

N⁶,5-dibenzoyl-2'-deoxy-8-[(4,4'-dimethoxytrityloxy)methyl]adenosine

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