N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Base Information

• Chemical Name: N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine
• CAS No.: 1376827-47-2
• Molecular Formula: C₃₀H₄₆N₆O₈Si₂
• Molecular Weight: 674.902
• Mol file: 1376827-47-2.mol

Synonyms:N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Chemical Property of N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

There total 5 articles about N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine 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: 55.0%

2-nitrobenzylcarbonylimidazole + 5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-52-9) → N(2)-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-47-2)

Guidance literature:

5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine; With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

2-nitrobenzylcarbonylimidazole; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1002/anie.201108018

Reference yield:

2-Nitrobenzyl alcohol (612-25-9) → N(2)-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran / 0.17 h / 20 °C

2.2: 3 h / 20 °C

With 18-crown-6 ether; sodium hydride; In tetrahydrofuran;

DOI:10.1002/anie.201108018

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N(2)-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / -10 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / -20 - 20 °C

3.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran / 0.17 h / 20 °C

3.2: 3 h / 20 °C

With 1H-imidazole; 18-crown-6 ether; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/anie.201108018

upstream raw materials:

5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

2-Nitrobenzyl alcohol

2'-Deoxyguanosine

tert-butyldimethylsilyl chloride

Downstream raw materials:

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-hydroxyethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-2'-deoxyguanosine