2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

Base Information

• Chemical Name: 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine
• CAS No.: 199792-80-8
• Molecular Formula: C₂₇H₃₈N₆O₇Si
• Molecular Weight: 586.72
• Mol file: 199792-80-8.mol

Synonyms:2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

Chemical Property of 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

There total 1 articles about 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 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: 77.0%

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) + 2'-deoxy-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (88091-69-4) → 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (199792-80-8) + 2'-deoxy-3',5'-bis-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

Guidance literature:

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

DOI:10.1080/07328319708006249

Reference yield: 96.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (199792-80-8) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (199792-91-1)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1080/07328319708006249

Reference yield:

2'-deoxy-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine (199792-80-8) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N6-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(2-cyanoethyl diisopropylphosphoramidite) (199793-03-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / pyridine / 2 h / 60 °C

2: 96 percent / (Bu₄N)F*H₂O; AcOH / tetrahydrofuran / 288 h / 20 °C

3: 90 percent / 1H-tetrazole / acetonitrile / 1 h

With pyridine; 1H-tetrazole; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; acetonitrile; 1: Condensation / 2: desilylation / 3: phosphitylation;

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-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

Downstream raw materials:

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(hydrogen butanedioate)

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N⁶-{[2-(4-nitrophenyl)ethoxy]carbonyl}adenosine 5'-(2-cyanoethyl diisopropylphosphoramidite)