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

Base Information

• Chemical Name: 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
• CAS No.: 917474-26-1
• Molecular Formula: C₄₈H₆₀N₈O₁₆Si₂
• Molecular Weight: 1061.22

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 10 articles about 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 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: 94.0%

O6-[2-(4-nitrophenyl)ethyl]-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]guanine (917376-79-5) + 1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride (88091-70-7) → 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 (917474-26-1)

Guidance literature:

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

DOI:10.1080/15257770500267113

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → 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 (917474-26-1)

Guidance literature:

Multi-step reaction with 8 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

7: 83 percent / pyridine / 24 h / 20 °C

8: 94 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

With pyridine; hydrogenchloride; dmap; 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-{3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine (917474-26-1)

Guidance literature:

Multi-step reaction with 8 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

7: 83 percent / pyridine / 24 h / 20 °C

8: 94 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

With pyridine; hydrogenchloride; dmap; 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-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]guanine

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

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

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

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-{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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