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

Base Information

• Chemical Name: N⁴-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine
• CAS No.: 1447969-96-1
• Molecular Formula: C₄₃H₄₄N₄O₁₂
• Molecular Weight: 808.842

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about N⁴-acetyl-5’-O-(4,4’-dimethoxytrityl)-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: 90.1%

N4-acetyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-94-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N4-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-96-1)

Guidance literature:

With pyridine; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.06.001

Reference yield:

N4-acetyl-3’, 5’-O-di-tert-silyl-2’-O-[(methylthio)methyl]cytidine (1447969-90-5) → N4-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-96-1)

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 / Inert atmosphere

3: pyridine / 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:

N4-acetyl-3’,5’-O-di-tert-silyl-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-93-8) → N4-acetyl-5’-O-(4,4’-dimethoxytrityl)-2’-O-[[2-methyl-2-(2-nitrophenyl)-1-oxopropoxy]methyl]cytidine (1447969-96-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: pyridine / 20 °C / Inert atmosphere

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

DOI:10.1016/j.tetlet.2013.06.001

upstream raw materials:

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

4,4'-dimethoxytrityl chloride

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

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

Downstream raw materials:

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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