O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine

Base Information

• Chemical Name: O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine
• CAS No.: 917376-77-3
• Molecular Formula: C₃₀H₄₆N₆O₈Si₂
• Molecular Weight: 674.902

Synonyms:O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine

Chemical Property of O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine

Chemical Property:

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Technology Process of O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine

There total 8 articles about O⁶-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-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: 77.0%

O6-[2-(4-nitrophenyl)ethyl]-9-(α-D-arabinofuranosyl)guanine (917376-72-8) + 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine (917376-77-3)

Guidance literature:

With pyridine; at 20 ℃; for 18h;

DOI:10.1080/15257770500267113

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine (917376-77-3)

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: 85 percent / K₂CO₃ / methanol / 2 h / Heating

6: 77 percent / pyridine / 18 h / 20 °C

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

DOI:10.1080/15257770500267113

Reference yield:

2,9-diacetylguanine (3056-33-5) → O6-[2-(4-nitrophenyl)ethyl]-9-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-α-D-arabinofuranosyl]guanine (917376-77-3)

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: 85 percent / K₂CO₃ / methanol / 2 h / Heating

6: 77 percent / pyridine / 18 h / 20 °C

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

DOI:10.1080/15257770500267113

upstream raw materials:

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

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

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

2-(4-nitrophenyl)ethanol

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