N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine

Base Information

• Chemical Name: N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine
• CAS No.: 1312690-32-6
• Molecular Formula: C₅₄H₆₇N₅O₁₁Si
• Molecular Weight: 990.238

Synonyms:N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine

Chemical Property of N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine

Chemical Property:

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Technology Process of N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine

There total 10 articles about N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-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: 28.0%

N6-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-adenosine (1312690-34-8) + iodomethyl pivaloate (53064-79-2) → N6-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine (1312690-32-6)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In 1,2-dichloro-ethane; at 75 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo200826h

Reference yield:

5'-O-dimethoxytrityladenosine (57018-82-3,81352-25-2) → N6-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine (1312690-32-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; dmap; triethylamine / 0.5 h / 20 °C / Inert atmosphere

2: pyridine; phosgene; dmap / dichloromethane; toluene / 20 °C

3: triethylamine / dichloromethane; toluene / 36 h / 20 °C

4: ethanol; sodium hydroxide / 1 h / 20 °C

5: tetrabutylammomium bromide; di(n-butyl)tin oxide / 1,2-dichloro-ethane / 2 h / 75 °C / Inert atmosphere

With pyridine; phosgene; dmap; ethanol; tetrabutylammomium bromide; di(n-butyl)tin oxide; triethylamine; sodium hydroxide; In dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo200826h

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine (151928-74-4) → N6-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-adenosine (1312690-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; phosgene; dmap / dichloromethane; toluene / 20 °C

2: triethylamine / dichloromethane; toluene / 36 h / 20 °C

3: ethanol; sodium hydroxide / 1 h / 20 °C

4: tetrabutylammomium bromide; di(n-butyl)tin oxide / 1,2-dichloro-ethane / 2 h / 75 °C / Inert atmosphere

With pyridine; phosgene; dmap; ethanol; tetrabutylammomium bromide; di(n-butyl)tin oxide; triethylamine; sodium hydroxide; In dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo200826h

upstream raw materials:

5'-O-dimethoxytrityladenosine

5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine

N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine

N₆-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-adenosine

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