N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine
• CAS No.: 329188-29-6
• Molecular Formula: C₅₄H₇₀N₇O₁₉PSi₂
• Molecular Weight: 1208.33

Synonyms:N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

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Technology Process of N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

There total 2 articles about N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]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: 72.0%

bis(p-nitrophenylethyl)phosphate triethylammonium salt + N6-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-28-5) → N6-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-29-6)

Guidance literature:

With 1-methyl-1H-imidazole; Triphenylsilyl chloride; In pyridine; at 20 ℃; for 16h;

DOI:10.1080/15257770008045465

Reference yield:

N6-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-(4-methoxytrityl)-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-22-9) → N6-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / CF₃CO₂H / CHCl₃ / 0.17 h / 20 °C

2: 72 percent / 1-methylimidazole; TPSCl / pyridine / 16 h / 20 °C

With 1-methyl-1H-imidazole; Triphenylsilyl chloride; trifluoroacetic acid; In pyridine; chloroform;

DOI:10.1080/15257770008045465

Reference yield: 59.0%

N6-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-29-6) → N6-benzoyl-9-[2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (329188-30-9)

Guidance literature:

N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.25h;

With Dowex-50 (Na⁺-form); In tetrahydrofuran; water; at 20 ℃; for 0.5h;

DOI:10.1080/15257770008045465

upstream raw materials:

N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

N⁶-benzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3-di-O-acetyl-5-O-(4-methoxytrityl)-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

Downstream raw materials:

N⁶-benzoyl-9-[2-O-(2,3-di-O-acetyl-5-O-bis(p-nitrophenylethyl)phosphorylyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

O-β-D-ribofuranosyl-(1''-2')-adenosine-5''-O-phosphate

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