N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanine

Base Information

• Chemical Name: N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanine
• CAS No.: 908371-60-8
• Molecular Formula: C₃₃H₄₇F₃N₆O₁₁SSi₂
• Molecular Weight: 849.002

Synonyms:N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanine

Chemical Property of N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanine

Chemical Property:

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Technology Process of N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanine

There total 6 articles about N²-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O⁶-[2-(4-nitrophenyl)ethyl]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: 69.0%

N2-acetyl-9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]-O6-[2-(4-nitrophenyl)ethyl]guanine (908371-55-1) + trifluoromethane sulfonyl chloride (421-83-0) → N2-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O6-[2-(4-nitrophenyl)ethyl]guanine (908371-60-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja0621400

Reference yield:

9-β-D-arabinofuranosylguanine (38819-10-2) → N2-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O6-[2-(4-nitrophenyl)ethyl]guanine (908371-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / pyridine / dimethylformamide / 16 h / 20 °C

2.1: 2.91 g / pyridine / dimethylformamide / 16 h / 80 °C

3.1: triphenylphosphine / dioxane / 0.5 h

3.2: 64 percent / diisopropyl azodicarboxylate / dioxane / 0.75 h

4.1: 57 percent / aq. NaOH / tetrahydrofuran; methanol / 0.12 h / 0 °C

5.1: 69 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

With pyridine; dmap; sodium hydroxide; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0621400

Reference yield:

N2-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine (908371-51-7) → N2-acetyl-9-{2'-O-[(trifluoromethyl)sulfonyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl}-O6-[2-(4-nitrophenyl)ethyl]guanine (908371-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine / dioxane / 0.5 h

1.2: 64 percent / diisopropyl azodicarboxylate / dioxane / 0.75 h

2.1: 57 percent / aq. NaOH / tetrahydrofuran; methanol / 0.12 h / 0 °C

3.1: 69 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; sodium hydroxide; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ja0621400

upstream raw materials:

N²-acetyl-9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanine

trifluoromethane sulfonyl chloride

N²-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine

N²-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanine

Downstream raw materials:

N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoguanosine

N²-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-O⁶-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2'-methylselenoguanosine

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