O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine

Base Information

• Chemical Name: O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine
• CAS No.: 917376-76-2
• Molecular Formula: C₂₇H₂₇N₇O₁₁
• Molecular Weight: 625.552

Synonyms:O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine

Chemical Property of O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine

Chemical Property:

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Technology Process of O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine

There total 8 articles about O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine 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: 81.0%

O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)guanine (917376-75-1) → O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine (917376-76-2)

Guidance literature:

With ammonia; In 1,4-dioxane; methanol; water; at 20 ℃; for 48h;

DOI:10.1080/15257770500267113

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine (917376-76-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / triphenylphosphine; ethyl azodicarboxylate / dioxane / 24 h

2: 69 percent / HCl / methanol / 48 h / 20 °C

3: CH₂Cl₂ / 2 h / 80 °C

4: 14.6 g / trimethylsilyl trifluorosulfonate / toluene / 8 h / 80 °C

5: 93 percent / pyridine / 48 h / cooling

6: 81 percent / NH₃ / H₂O; methanol; dioxane / 48 h / 20 °C

With pyridine; hydrogenchloride; ethyl azodicarboxylate; trimethylsilyl trifluorosulfonate; ammonia; triphenylphosphine; In 1,4-dioxane; methanol; dichloromethane; water; toluene;

DOI:10.1080/15257770500267113

Reference yield:

2,9-diacetylguanine (3056-33-5) → O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(α-D-arabinofuranosyl)guanine (917376-76-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / triphenylphosphine; ethyl azodicarboxylate / dioxane / 24 h

2: 69 percent / HCl / methanol / 48 h / 20 °C

3: CH₂Cl₂ / 2 h / 80 °C

4: 14.6 g / trimethylsilyl trifluorosulfonate / toluene / 8 h / 80 °C

5: 93 percent / pyridine / 48 h / cooling

6: 81 percent / NH₃ / H₂O; methanol; dioxane / 48 h / 20 °C

With pyridine; hydrogenchloride; ethyl azodicarboxylate; trimethylsilyl trifluorosulfonate; ammonia; triphenylphosphine; In 1,4-dioxane; methanol; dichloromethane; water; toluene;

DOI:10.1080/15257770500267113

upstream raw materials:

O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)guanine

O⁶-[2-(4-nitrophenyl)ethyl]-9-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)guanine

2-(4-nitrophenyl)ethanol

2,9-diacetylguanine

Downstream raw materials:

O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine

O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine

O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine

O⁶-[2-(4-nitrophenyl)ethyl]-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-9-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine

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