1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one

Base Information

• Chemical Name: 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one
• CAS No.: 947251-95-8
• Molecular Formula: C₂₈H₄₅N₃O₆Si₂
• Molecular Weight: 575.853
• Mol file: 947251-95-8.mol

Synonyms:1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one

Chemical Property of 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one

There total 4 articles about 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one 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: 59.0%

3',5'-bis-O-(tert-butyldimethylsilyl)-O4-[(2,4,6-trimethylphenyl)sulfonyl]thymidine (947251-79-8) + m-nitrobenzene boronic acid (13331-27-6) → 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one (947251-95-8) + 3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4)

Guidance literature:

With potassium phosphate; CyJohnPhos; In various solvent(s); at 50 ℃; for 15h;

DOI:10.1021/jo070843+

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one (947251-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 24 h / 20 °C

2: 89 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 31 h / 0 - 20 °C

3: 59 percent / potassium phosphate; 2-dicyclohexylphosphinobiphenyl / various solvent(s) / 15 h / 50 °C

With 1H-imidazole; dmap; potassium phosphate; triethylamine; CyJohnPhos; In dichloromethane; N,N-dimethyl-formamide; 3: Suzuki-Miyaura reaction;

DOI:10.1021/jo070843+

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one (947251-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 31 h / 0 - 20 °C

2: 59 percent / potassium phosphate; 2-dicyclohexylphosphinobiphenyl / various solvent(s) / 15 h / 50 °C

With dmap; potassium phosphate; triethylamine; CyJohnPhos; In dichloromethane; 2: Suzuki-Miyaura reaction;

DOI:10.1021/jo070843+

upstream raw materials:

3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine

m-nitrobenzene boronic acid

tert-butyldimethylsilyl chloride

3',5'-O-di(tert-butyldimethylsilyl)thymidine