N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine

Base Information

• Chemical Name: N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine
• CAS No.: 1312690-17-7
• Molecular Formula: C₃₆H₅₉N₃O₈SSi₂
• Molecular Weight: 750.117

Synonyms:N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine

Chemical Property of N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine

There total 7 articles about N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine 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: 61.0%

N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-cytidine (1312690-16-6) + dimethyl sulfoxide (67-68-5,8070-53-9) → N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine (1312690-17-7)

Guidance literature:

With acetic anhydride; In acetic acid; at 35 ℃; for 24h;

DOI:10.1021/jo200826h

Reference yield:

salicylic alcohol (90-01-7) → N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine (1312690-17-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 4 °C

1.2: -55 °C

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.83 h / 0 - 20 °C / Inert atmosphere

3.1: 1-methyl-1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: ethanol; sodium hydroxide / 2 h / 20 °C

5.1: silver nitrate / N,N-dimethyl-formamide / 0 - 20 °C

6.1: acetic anhydride / acetic acid / 24 h / 35 °C

With 1-methyl-1H-imidazole; ethanol; acetic anhydride; sodium hydride; silver nitrate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo200826h

Reference yield:

triisopropylsilyl chloride (13154-24-0) → N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-methylthiomethyl-cytidine (1312690-17-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 4 °C

1.2: -55 °C

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.83 h / 0 - 20 °C / Inert atmosphere

3.1: 1-methyl-1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: ethanol; sodium hydroxide / 2 h / 20 °C

5.1: silver nitrate / N,N-dimethyl-formamide / 0 - 20 °C

6.1: acetic anhydride / acetic acid / 24 h / 35 °C

With 1-methyl-1H-imidazole; ethanol; acetic anhydride; sodium hydride; silver nitrate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo200826h

upstream raw materials:

N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-cytidine

dimethyl sulfoxide

2-[(triisopropylsilyl)oxy]-benzyl carbonochloridate

N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2',3',5'-tri-O-acetyl-cytidine

Downstream raw materials:

N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-3',5'-O-di-tert-butylsilanediyl-2'-O-pivaloyloxymethyl-cytidine

C₃₂H₄₉N₃O₁₀Si

N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-cytidine

N₄-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-cytidine

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