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

Base Information

• Chemical Name: N²-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine
• CAS No.: 1447969-83-6
• Molecular Formula: C₃₅H₅₂N₆O₁₁Si₂
• Molecular Weight: 789.002

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

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

Chemical Property:

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• Pictogram(s):  
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Technology Process of N²-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine

There total 2 articles about N²-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-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: 50.1%

potassium 2,2-dimethyl-2-(2-nitrophenyl)acetate (126802-51-5) + N2-acetyl-3’,5’-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2’-O-[(methylthio)methyl]guanosine (1447969-82-5) → 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)

Guidance literature:

With 18-crown-6 ether; bromine; trimethylsilylacetylene; In 1,2-dichloro-ethane; for 1h; Cooling with ice; 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)guanosine (847979-69-5) → 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)

Guidance literature:

Multi-step reaction with 2 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

With 18-crown-6 ether; bromine; acetic anhydride; acetic acid; trimethylsilylacetylene; In 1,2-dichloro-ethane; 1: |Pummerer Sulfoxide Rearrangement;

DOI:10.1016/j.tetlet.2013.06.001

Reference yield: 100.0%

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-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]guanosine (1447969-84-7)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

potassium 2,2-dimethyl-2-(2-nitrophenyl)acetate

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)guanosine

Downstream raw materials:

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

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

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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