N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

Base Information

• Chemical Name: N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine
• CAS No.: 158813-60-6
• Molecular Formula: C₃₉H₅₁N₃O₅Si₂
• Molecular Weight: 698.022

Synonyms:N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

Chemical Property of N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

There total 4 articles about N⁴-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine 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: 96.0%

benzamide (55-21-0,27208-38-4) + 5'-O-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine (158813-59-3) → N4-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine (158813-60-6)

Guidance literature:

With sodium hydride; In 1,4-dioxane; 1.) r.t., 1 h, 2.) r.t., 2 h;

DOI:10.1021/jo00121a037

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N4-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine (158813-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 1.) POCl₃, Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) r.t., 3 h

3: 96 percent / NaH / dioxane / 1.) r.t., 1 h, 2.) r.t., 2 h

With 1H-imidazole; sodium hydride; triethylamine; trichlorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a037

Reference yield:

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → N4-Benzoyl-5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine (158813-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 1.) POCl₃, Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) r.t., 3 h

3: 96 percent / NaH / dioxane / 1.) r.t., 1 h, 2.) r.t., 2 h

With 1H-imidazole; sodium hydride; triethylamine; trichlorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a037

upstream raw materials:

benzamide

5'-O-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine

tert-butylchlorodiphenylsilane

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Downstream raw materials:

5'-O-Phthalimido-N⁴-benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine

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