N²-acetyl-9-[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-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanine
• CAS No.: 908371-55-1
• Molecular Formula: C₃₂H₄₈N₆O₉Si₂
• Molecular Weight: 716.939
• Mol file: 908371-55-1.mol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about N²-acetyl-9-[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: 57.0%

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) → 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)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 0.116667h;

DOI:10.1021/ja0621400

Reference yield:

9-β-D-arabinofuranosylguanine (38819-10-2) → 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)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; sodium hydroxide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; 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-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]-O6-[2-(4-nitrophenyl)ethyl]guanine (908371-55-1)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/ja0621400

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

9-β-D-arabinofuranosylguanine

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

Downstream raw materials:

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

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

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