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

Base Information

• Chemical Name: N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine
• CAS No.: 1376827-51-8
• Molecular Formula: C₅₀H₅₆ClN₈O₁₁P
• Molecular Weight: 1011.47

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 11 articles about N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-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:

N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5'-O-dimethoxytrityl-2'-deoxyguanosine (1376827-54-1) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine (1376827-51-8)

Guidance literature:

With 5-(ethylthio)-1H-tetrazole; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1002/anie.201108018

Reference yield:

N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-53-0) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine (1376827-51-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Quinuclidine / tetrahydrofuran / 1 h / 20 °C

1.2: 3 h / 0 °C

2.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C

2.2: 0.33 h / 0 °C

3.1: tetrabutyl ammonium fluoride; toluene-4-sulfonic acid / tetrahydrofuran; methanol; water / 26 h / 0 - 20 °C

4.1: pyridine / 2 h / 20 °C

5.1: 5-(ethylthio)-1H-tetrazole / dichloromethane / 0.33 h / 20 °C

With Quinuclidine; pyridine; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 5-(ethylthio)-1H-tetrazole; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/anie.201108018

Reference yield:

N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-hydroxyethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-48-3) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine (1376827-51-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C

1.2: 0.33 h / 0 °C

2.1: tetrabutyl ammonium fluoride; toluene-4-sulfonic acid / tetrahydrofuran; methanol; water / 26 h / 0 - 20 °C

3.1: pyridine / 2 h / 20 °C

4.1: 5-(ethylthio)-1H-tetrazole / dichloromethane / 0.33 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 5-(ethylthio)-1H-tetrazole; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/anie.201108018

upstream raw materials:

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

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

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