5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate

Base Information

• Chemical Name: 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate
• CAS No.: 118149-31-8
• Molecular Formula: C₄₃H₄₇N₄O₁₄PS
• Molecular Weight: 906.904
• Mol file: 118149-31-8.mol

Synonyms:5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate

Chemical Property of 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate

There total 29 articles about 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate 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: 87.0%

O-<5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl> O-(3'-O-acetylthymidin-5'-yl) hydrogenphosphonothioate (118149-24-9) → 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate (118149-31-8)

Guidance literature:

With iodine; In pyridine; water;

DOI:10.1016/0040-4039(88)85045-7

Reference yield: 85.0%

O-methyl bis(O-4-nitrophenyl)phosphite + 3'-O-acetylthymidine (21090-30-2) + 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → para-methoxynitrobenzene (100-17-4) + 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate (118149-31-8)

Guidance literature:

O-methyl bis(O-4-nitrophenyl)phosphite; 5'-O-(4-4'-dimethoxytrityl)thymidine; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

3'-O-acetylthymidine; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With sulfur; In diisopropylamine; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.06.102

Reference yield:

5‘-O-dimethoxytrityl-2’-deoxyribothymidine 3‘-O-phosphorodiamidite (104655-84-7) → 5'-O-dimethoxytritylthimidine-3'-O-(5'-O-thymidylyl-3'-O-acetyl)phosphorothioate (118149-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent

2: 90 percent / 1.) H₂S; 2.) tetrazole / acetonitrile / 1.) 1 min; 2.) 16 h, sealed flask

3: 87 percent / iodine / H₂O; pyridine

With 1H-tetrazole; hydrogen sulfide; iodine; In pyridine; water; acetonitrile;

DOI:10.1016/0040-4039(88)85045-7

upstream raw materials:

O-<5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl> O-(3'-O-acetylthymidin-5'-yl) hydrogenphosphonothioate

triethylammonium acetate

3'-O-acetylthymidine

5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]phosphinyl]thymidine

Downstream raw materials:

C₄₁H₄₅N₄O₁₃PS