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)

Base Information

• Chemical Name: 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)
• CAS No.: 1447969-88-1
• Molecular Formula: C₅₃H₆₁N₈O₁₃P
• Molecular Weight: 1049.09

Synonyms: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)

Chemical Property of 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)

Chemical Property:

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Technology Process of 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)

There total 4 articles about 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) 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: 76.5%

N2-acetyl-5’-O-(4, 4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-86-9) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 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) (1447969-88-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; 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-3’-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (1447969-88-1)

Guidance literature:

Multi-step reaction with 4 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

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 18-crown-6 ether; bromine; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; trimethylsilylacetylene; In tetrahydrofuran; dichloromethane; 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)guanosine (847979-69-5) → 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) (1447969-88-1)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid; acetic anhydride / 48 h / 20 °C

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

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

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

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 18-crown-6 ether; bromine; acetic anhydride; acetic acid; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; trimethylsilylacetylene; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1: |Pummerer Sulfoxide Rearrangement;

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

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

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

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

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