2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

Base Information

• Chemical Name: 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine
• CAS No.: 263709-12-2
• Molecular Formula: C₅₆H₇₃N₇O₁₂Si₂
• Molecular Weight: 1092.41

Synonyms:2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

Chemical Property of 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

Chemical Property:

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Technology Process of 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

There total 14 articles about 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)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: 90.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + C35H55N7O10Si2 → 2'-O-[(tert-butyl)dimethylsilyl]-N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine (263709-12-2)

Guidance literature:

With pyridine; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.202002929

Reference yield: 44.0%

tert-butyldimethylsilyl chloride (18162-48-6) + N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine (263709-10-0) → 2'-O-[(tert-butyl)dimethylsilyl]-N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine (263709-12-2)

Guidance literature:

With silver nitrate; In tetrahydrofuran; pyridine; at 20 ℃; for 17h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → 2'-O-[(tert-butyl)dimethylsilyl]-N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine (263709-12-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 63 percent / 17 h / 105 °C

2: 95 percent / pyridine; 1H-imidazole / 17 h / 20 °C

3: toluene / 17 h / 80 °C

4: 100 percent / NH₃ / methanol / 3 h / 20 °C

5: 94 percent / pyridine / CH₂Cl₂ / 17 h / 20 °C

6: 44 percent / AgNO₃ / tetrahydrofuran; pyridine / 17 h / 20 °C

With pyridine; 1H-imidazole; ammonia; silver nitrate; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene; 1: Esterification / 2: Etherification / 3: Addition / 4: Deacetylation / 5: Etherification / 6: Etherification;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

upstream raw materials:

tert-butyldimethylsilyl chloride

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

2-(4-nitrophenyl)ethanol

4,4'-dimethoxytrityl chloride

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