N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

Base Information

• Chemical Name: N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine
• CAS No.: 1447969-86-9
• Molecular Formula: C₄₄H₄₄N₆O₁₂
• Molecular Weight: 848.866

Synonyms:N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

Chemical Property of N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

There total 4 articles about N²-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine 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: 99.6%

N2-acetyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-84-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N2-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-86-9)

Guidance literature:

With pyridine; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.06.001

Reference yield:

N2-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[(methylthio)methyl]guanosine (1447969-82-5) → N2-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-86-9)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine; trimethylsilylacetylene; 18-crown-6 ether / 1,2-dichloro-ethane / 1 h / Cooling with ice; Inert atmosphere

2: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 3 h / Inert atmosphere

3: pyridine / 3 h / 20 °C / Inert atmosphere

With pyridine; 18-crown-6 ether; bromine; triethylamine tris(hydrogen fluoride); trimethylsilylacetylene; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1016/j.tetlet.2013.06.001

Reference yield:

N2-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-83-6) → N2-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 3 h / Inert atmosphere

2: pyridine / 3 h / 20 °C / Inert atmosphere

With pyridine; triethylamine tris(hydrogen fluoride); In tetrahydrofuran;

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

N²-acetyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

4,4'-dimethoxytrityl chloride

N²-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[(methylthio)methyl]guanosine

N²-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

Downstream raw materials:

N²-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine-3’-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

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