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

Base Information

• Chemical Name: N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine
• CAS No.: 1376827-53-0
• Molecular Formula: C₄₅H₆₈N₆O₁₀SSi₂
• Molecular Weight: 941.306

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

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

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

There total 7 articles about N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2,4,6-triisopropylphenylsulfonyl)-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: 81.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + N(2)-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-47-2) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-53-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/anie.201108018

Reference yield:

2-nitrobenzylcarbonylimidazole → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran / 0.17 h / 20 °C

1.2: 3 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C

With dmap; 18-crown-6 ether; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201108018

Reference yield:

2-Nitrobenzyl alcohol (612-25-9) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-53-0)

Guidance literature:

Multi-step reaction with 3 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

3.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C

With dmap; 18-crown-6 ether; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201108018

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

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

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

2-Nitrobenzyl alcohol

Downstream raw materials:

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)-5'-O-dimethoxytrityl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine

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

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