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

Base Information

• Chemical Name: 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-uridine
• CAS No.: 1373621-12-5
• Molecular Formula: C₄₂H₅₄N₂O₁₀Si
• Molecular Weight: 775.973

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

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

Chemical Property:

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

There total 4 articles about 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-¹³C-uridine 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: 82.0%

5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-10-3) + acetic anhydride (108-24-7) → 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-12-5)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja302148g

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 5 h / 20 °C / Inert atmosphere

2.1: dibutyltin chloride; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 1 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 80 °C / Inert atmosphere

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

With pyridine; dmap; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane;

DOI:10.1021/ja302148g

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-6-13C-uridine (1373621-06-7) → 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropylsilyl)oxy]methyl]-6-13C-uridine (1373621-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin chloride; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 1 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 80 °C / Inert atmosphere

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

With pyridine; dmap; dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane;

DOI:10.1021/ja302148g

upstream raw materials:

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

acetic anhydride

6-¹³C-uridine

5'-O-(4,4'-dimethoxytrityl)-6-¹³C-uridine

Downstream raw materials:

N⁴-acetyl-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 3'-O-(2'-cyanoethyl N,N-diisopropylphoshphoramidite)

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

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