2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Base Information

• Chemical Name: 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine
• CAS No.: 199792-82-0
• Molecular Formula: C₃₅H₄₅N₇O₁₀Si
• Molecular Weight: 751.869

Synonyms:2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property of 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property:

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Safty Information:

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Technology Process of 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

There total 1 articles about 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 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: 75.0%

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) + 2'-deoxy-N2-[2-(4-nitrophenyl)ethoxycarbonyl]-O6-[2-(4-nitrophenyl)ethyl]guanosine (111244-92-9) → 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199792-82-0) + 2'-deoxy-3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1080/07328319708006249

Reference yield: 95.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199792-82-0) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199792-92-2)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1080/07328319708006249

Reference yield:

2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199792-82-0) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199793-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 2 h / 60 °C

2: 95 percent / (Bu₄N)F*H₂O; AcOH / tetrahydrofuran / 288 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; 1: Condensation / 2: desilylation;

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

upstream raw materials:

chlorodimethyl(1,1,2-trimethylpropyl)silane

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

Downstream raw materials:

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

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

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

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