N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine

Base Information

• Chemical Name: N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine
• CAS No.: 166758-09-4
• Molecular Formula: C₄₀H₃₈N₄O₇Si
• Molecular Weight: 714.85
• Mol file: 166758-09-4.mol

Synonyms:N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine

Chemical Property of N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine

There total 3 articles about N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine 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:

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) → N4-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine (166758-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 60 percent / CCl₃CO₂H / CH₂Cl₂ / 3 h / Ambient temperature

3: Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a037

Reference yield:

4-N-benzoyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O-dimethoxytritylcytidine (166758-07-2) → N4-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine (166758-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / CCl₃CO₂H / CH₂Cl₂ / 3 h / Ambient temperature

2: Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature

With di-isopropyl azodicarboxylate; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00121a037

Reference yield:

N-hydroxyphthalimide (524-38-9) + 3'-O-tert-butydiphenylsilyl-N4-benzoyl-2'-deoxycytidine (166758-08-3) → N4-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine (166758-09-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 16h; Yield given; Ambient temperature;

DOI:10.1021/jo00121a037

upstream raw materials:

N-hydroxyphthalimide

3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

4-N-benzoyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O-dimethoxytritylcytidine

Downstream raw materials:

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