N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine

Base Information

• Chemical Name: N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine
• CAS No.: 917376-51-3
• Molecular Formula: C₂₈H₂₇N₇O₁₂
• Molecular Weight: 653.562

Synonyms:N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine

Chemical Property of N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine

There total 6 articles about N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine 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: 82.0%

N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}adenine (917376-43-3) → N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-51-3)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1080/15257770500267113

Reference yield:

N-benzoyladenine (4005-49-6) → N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-51-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,2-dichloro-ethane / 0.25 h / 80 °C

2: 1.48 g / trimethylsilyl trifluorosulfonate; SnCl₄ / acetonitrile / 20 h / 20 °C

3: 67 percent / NH₃ / methanol / 28 h / 20 °C

4: 83 percent / pyridine / 15 h / 20 °C

5: 92 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

6: 82 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluorosulfonate; tetrabutyl ammonium fluoride; ammonia; tin(IV) chloride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1080/15257770500267113

Reference yield:

N6-benzoyl-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)adenine (56517-36-3) → N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / NH₃ / methanol / 28 h / 20 °C

2: 83 percent / pyridine / 15 h / 20 °C

3: 92 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

4: 82 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; ammonia; acetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1080/15257770500267113

upstream raw materials:

N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}adenine

N⁶-benzoyl-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)adenine

9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]adenine

N-benzoyladenine

Downstream raw materials:

N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine

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