N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)

Base Information

• Chemical Name: N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)
• CAS No.: 1373621-19-2
• Molecular Formula: C₅₁H₇₂N₅O₁₀PSi
• Molecular Weight: 975.208

Synonyms:N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)

Chemical Property of N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)

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Technology Process of N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)

There total 8 articles about N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite) 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:

N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-cytidine (1373621-16-9) + bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0) → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite) (1373621-19-2)

Guidance literature:

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine; With N,N-dimethyl-ethanamine; In dichloromethane; at 20 ℃; for 0.25h;

bis(2-cyanoethyl) diisopropylamidophosphite; In dichloromethane; for 2h;

DOI:10.1016/bs.mie.2015.06.013

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-10-3) → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite) (1373621-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; dmap / 2 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 0.17 h / Inert atmosphere

2.2: 4 h / Inert atmosphere

3.1: ammonia / tetrahydrofuran; water / 18 h / 20 °C / Inert atmosphere

4.1: N,N-dimethyl-ethanamine / dichloromethane / 0.25 h / Inert atmosphere

4.2: 2 h / Inert atmosphere

With pyridine; dmap; N,N-dimethyl-ethanamine; ammonia; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja302148g

Reference yield:

3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-12-5) → N4-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-cytidine 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite) (1373621-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 0.17 h / Inert atmosphere

1.2: 4 h / Inert atmosphere

2.1: ammonia / tetrahydrofuran; water / 18 h / 20 °C / Inert atmosphere

3.1: N,N-dimethyl-ethanamine / dichloromethane / 0.25 h / Inert atmosphere

3.2: 2 h / Inert atmosphere

With dmap; N,N-dimethyl-ethanamine; ammonia; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja302148g

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-uridine

3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-uridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-cytidine

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