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

Base Information

• Chemical Name: 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
• CAS No.: 917376-43-3
• Molecular Formula: C₄₀H₅₃N₇O₁₃Si₂
• Molecular Weight: 896.071

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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%

1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride (88091-70-7) + 9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]adenine (87792-05-0) → 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)

Guidance literature:

With dmap; In dichloromethane; at 5 ℃; for 18h;

DOI:10.1080/15257770500267113

Reference yield:

N-benzoyladenine (4005-49-6) → 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)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; trimethylsilyl trifluorosulfonate; ammonia; tin(IV) chloride; In 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]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}adenine (917376-43-3)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; dmap; ammonia; In methanol; dichloromethane;

DOI:10.1080/15257770500267113

upstream raw materials:

1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride

9-[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

N-benzoyladenine

Downstream raw materials:

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

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

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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