N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

Base Information

• Chemical Name: N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine
• CAS No.: 1447969-81-4
• Molecular Formula: C₃₆H₄₄N₆O₉Si
• Molecular Weight: 732.866

Synonyms:N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

Chemical Property of N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

There total 2 articles about N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine 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: 85.9%

potassium 2,2-dimethyl-2-(2-nitrophenyl)acetate (126802-51-5) + N6-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[(methylthio)methyl]adenosine (1447969-80-3) → N6-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine (1447969-81-4)

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:

N6-benzoyl-3’,5’-O-di-tert-butylsilyl adenosine (148692-01-7) → N6-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine (1447969-81-4)

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%

N6-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine (1447969-81-4) → N6-benzoyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine (923291-09-2)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

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

N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl-2’-O-[(methylthio)methyl]adenosine

N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl adenosine

Downstream raw materials:

N⁶-benzoyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

N⁶-benzoyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine

N⁶-benzoyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]adenosine-3’-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

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