2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)

Base Information

• Chemical Name: 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)
• CAS No.: 199793-06-1
• Molecular Formula: C₄₄H₄₂N₆O₁₂
• Molecular Weight: 846.85

Synonyms:2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)

Chemical Property of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)

There total 7 articles about 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate) 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: 92.0%

succinic acid anhydride (108-30-5) + 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (199793-00-5) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate) (199793-06-1)

Guidance literature:

With dmap; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1080/07328319708006249

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate) (199793-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine / CH₂Cl₂ / 32 h / 20 °C

2: 95 percent / DBU / acetonitrile / 0.02 h / 20 °C

3: 89 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; 1: Condensation / 2: Elimination / 3: Esterification;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

Reference yield:

2'-deoxy-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (88091-69-4) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate) (199793-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / 1H-imidazole / dimethylformamide / 2 h / 20 °C

2: 96 percent / pyridine / 2 h / 60 °C

3: 96 percent / (Bu₄N)F*H₂O; AcOH / tetrahydrofuran / 288 h / 20 °C

4: 89 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Condensation / 3: desilylation / 4: Esterification;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

upstream raw materials:

succinic acid anhydride

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

4,4'-dimethoxytrityl chloride

2'-deoxy-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

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