2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)

Base Information

• Chemical Name: 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)
• CAS No.: 199793-04-9
• Molecular Formula: C₅₇H₆₂N₉O₁₃P
• Molecular Weight: 1112.15

Synonyms:2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property:

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Technology Process of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)

There total 7 articles about 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite) 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: 83.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199793-01-6) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite) (199793-04-9)

Guidance literature:

With 1H-tetrazole; In acetonitrile;

DOI:10.1080/07328319708006249

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite) (199793-04-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridine / CH₂Cl₂ / 32 h / 20 °C

2: 95 percent / DBU / acetonitrile / 0.02 h / 20 °C

3: 83 percent / 1H-tetrazole / acetonitrile / 1 h

With pyridine; 1H-tetrazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; 1: Condensation / 2: Elimination / 3: phosphitylation;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

Reference yield:

2'-deoxy-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-O6-[2-(4-nitrophenyl)ethyl]guanosine (111244-92-9) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite) (199793-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / 1H-imidazole / dimethylformamide / 2 h / 20 °C

2: 95 percent / pyridine / 2 h / 60 °C

3: 95 percent / (Bu₄N)F*H₂O; AcOH / tetrahydrofuran / 288 h / 20 °C

4: 83 percent / 1H-tetrazole / acetonitrile / 1 h

With pyridine; 1H-imidazole; 1H-tetrazole; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Condensation / 3: desilylation / 4: phosphitylation;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

upstream raw materials:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

4,4'-dimethoxytrityl chloride

2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

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