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

Base Information

• Chemical Name: N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine
• CAS No.: 917376-67-1
• Molecular Formula: C₄₉H₄₅N₇O₁₄
• Molecular Weight: 955.935

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

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

Chemical Property:

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

There total 7 articles about N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-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: 95.0%

N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-51-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-67-1)

Guidance literature:

With pyridine; at 20 ℃; for 40h;

DOI:10.1080/15257770500267113

Reference yield:

N-benzoyladenine (4005-49-6) → N6-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-67-1)

Guidance literature:

Multi-step reaction with 7 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

7: 95 percent / pyridine / 40 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-[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-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}adenine (917376-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 12 h / 20 °C

2: 95 percent / pyridine / 40 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1080/15257770500267113

upstream raw materials:

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

4,4'-dimethoxytrityl chloride

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

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