N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

Base Information

• Chemical Name: N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine
• CAS No.: 1447969-93-8
• Molecular Formula: C₃₀H₄₂N₄O₁₀Si
• Molecular Weight: 646.77

Synonyms:N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

Chemical Property of N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

There total 2 articles about N⁴-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine 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: 92.0%

potassium 2,2-dimethyl-2-(2-nitrophenyl)acetate (126802-51-5) + N4-acetyl-3’, 5’-O-di-tert-silyl-2’-O-[(methylthio)methyl]cytidine (1447969-90-5) → N4-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-93-8)

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:

N4-acetyl-3’,5’-O-di-tert-silyl cytidine (1245818-50-1) → N4-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; acetic anhydride / 72 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: 98.0%

N4-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-93-8) → N4-acetyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-94-9)

Guidance literature:

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

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

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

N⁴-acetyl-3’, 5’-O-di-tert-silyl-2’-O-[(methylthio)methyl]cytidine

N⁴-acetyl-3’,5’-O-di-tert-silyl cytidine

Downstream raw materials:

N⁴-acetyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

N⁴-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine

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

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