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

Base Information

• Chemical Name: 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
• CAS No.: 917376-86-4
• Molecular Formula: C₅₆H₅₀N₈O₁₆
• Molecular Weight: 1091.06

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 11 articles about 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 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:

2-(4-nitrophenyl)ethanol (100-27-6) → 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 (917376-86-4)

Guidance literature:

Multi-step reaction with 10 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

9: 80 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 3 h / 20 °C

10: 90 percent / pyridine / 20 h / 20 °C

With pyridine; hydrogenchloride; dmap; ethyl azodicarboxylate; trimethylsilyl trifluorosulfonate; tetrabutyl ammonium fluoride; ammonia; acetic acid; triphenylphosphine; In tetrahydrofuran; 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-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}guanine (917376-86-4)

Guidance literature:

Multi-step reaction with 10 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

9: 80 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 3 h / 20 °C

10: 90 percent / pyridine / 20 h / 20 °C

With pyridine; hydrogenchloride; dmap; ethyl azodicarboxylate; trimethylsilyl trifluorosulfonate; tetrabutyl ammonium fluoride; ammonia; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene;

DOI:10.1080/15257770500267113

Reference yield:

N2,N9-diacetyl-O6-2-(4-nitrophenyl)ethylguanine (917376-69-3) → 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 (917376-86-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / HCl / methanol / 48 h / 20 °C

2: CH₂Cl₂ / 2 h / 80 °C

3: 14.6 g / trimethylsilyl trifluorosulfonate / toluene / 8 h / 80 °C

4: 93 percent / pyridine / 48 h / cooling

5: 81 percent / NH₃ / H₂O; methanol; dioxane / 48 h / 20 °C

6: 83 percent / pyridine / 24 h / 20 °C

7: 94 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

8: 80 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 3 h / 20 °C

9: 90 percent / pyridine / 20 h / 20 °C

With pyridine; hydrogenchloride; dmap; trimethylsilyl trifluorosulfonate; tetrabutyl ammonium fluoride; ammonia; acetic acid; In tetrahydrofuran; 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-(α-D-arabinofuranosyl)guanine

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

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

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