5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine
• CAS No.: 504406-67-1
• Molecular Formula: C₅₄H₆₁N₅O₇Si
• Molecular Weight: 920.193

Synonyms:5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine

There total 6 articles about 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine 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: 30.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2-(4-phenylbutyl)adenosine (504406-64-8) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(4-phenylbutyl)adenosine (504406-67-1) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(4-phenylbutyl)adenosine

Guidance literature:

5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine; With 18-crown-6 ether; potassium hydride; In tetrahydrofuran; at 0 ℃;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at -78 ℃; Further stages.;

DOI:10.1021/ja021267w

Reference yield:

2-(4-phenyl-1-butyn-1-yl)adenosine (141345-16-6) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(4-phenylbutyl)adenosine (504406-67-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / atmospheric pressure

2.1: TMSCl; pyridine / 2 h / 20 °C

2.2: pyridine / 2.08 h / 0 - 20 °C

2.3: 83 percent / aq. NH₃ / pyridine / 0.25 h / 20 °C

3.1: 78 percent / pyridine

4.1: KH; 18-crown-6 / tetrahydrofuran / 0 °C

4.2: 30 percent / tetrahydrofuran / -78 °C

With pyridine; chloro-trimethyl-silane; 18-crown-6 ether; hydrogen; potassium hydride; 10 percent Pd/C; In tetrahydrofuran; ethanol;

DOI:10.1021/ja021267w

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(4-phenylbutyl)adenosine (504406-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / pyridine

2.1: KH; 18-crown-6 / tetrahydrofuran / 0 °C

2.2: 30 percent / tetrahydrofuran / -78 °C

With pyridine; 18-crown-6 ether; potassium hydride; In tetrahydrofuran;

DOI:10.1021/ja021267w

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-(4-phenylbutyl)adenosine

4,4'-dimethoxytrityl chloride

benzoyl chloride

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