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

Base Information

• Chemical Name: N²-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine
• CAS No.: 908371-51-7
• Molecular Formula: C₂₆H₄₃N₅O₈Si₂
• Molecular Weight: 609.827

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

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

Chemical Property:

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

There total 1 articles about N²-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-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:

9-β-D-arabinofuranosylguanine (38819-10-2) → N2-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine (908371-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine / dimethylformamide / 16 h / 20 °C

2: 2.91 g / pyridine / dimethylformamide / 16 h / 80 °C

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1021/ja0621400

Reference yield: 64.0%

N2-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine (908371-51-7) + 2-(4-nitrophenyl)ethanol (100-27-6) → 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 (908371-53-9)

Guidance literature:

N²-acetyl-9-[2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine; 2-(4-nitrophenyl)ethanol; With triphenylphosphine; In 1,4-dioxane; for 0.5h;

With di-isopropyl azodicarboxylate; In 1,4-dioxane; for 0.75h;

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-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoguanosine (908371-57-3)

Guidance literature:

Multi-step reaction with 6 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

4.1: sodium borohydride; ethanol / tetrahydrofuran / 1 h / 20 °C

4.2: 87 percent / tetrahydrofuran / 0.33 h / 20 °C

5.1: 79 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C

6.1: 59 percent / pyridine

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; ethanol; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ja0621400

upstream raw materials:

9-β-D-arabinofuranosylguanine

Downstream raw materials:

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

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

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

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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