5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 136681-22-6
• Molecular Formula: C₂₆H₃₀BrFN₂O₄Si
• Molecular Weight: 561.523
• Mol file: 136681-22-6.mol

Synonyms:

Chemical Property of 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

There total 9 articles about 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 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:

3'-fluoro-5'-O-tert-butyldiphenylsilyl-3'-deoxythymidine (116195-70-1) → 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (136681-22-6)

Guidance literature:

With bromine; In tetrachloromethane; for 1h; Heating; UV-irradiation;

DOI:10.1081/NCN-120027814

Reference yield:

3'-Fluoro-5'-O-trityl-deoxythymidine (135197-63-6) → 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (136681-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.28 g / aq. AcOH / 3 h / 25 °C

2: 90 percent / pyridine / 25 °C

3: Br₂ / CCl₄ / 1 h / Heating; UV-irradiation

With pyridine; bromine; acetic acid; In tetrachloromethane;

DOI:10.1081/NCN-120027814

Reference yield:

5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine (139212-95-6) → 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (136681-22-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / aq. sodium hydroxide / ethanol / 4 h / Heating

2: N,N-dimethylaminopyridine / dimethylformamide / 4 h / 50 °C

3: diethylaminosulfurtrifluoride / CH₂Cl₂ / 0 - 25 °C

4: 1.28 g / aq. AcOH / 3 h / 25 °C

5: 90 percent / pyridine / 25 °C

6: Br₂ / CCl₄ / 1 h / Heating; UV-irradiation

With pyridine; dmap; sodium hydroxide; diethylamino-sulfur trifluoride; bromine; acetic acid; In tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-120027814

upstream raw materials:

3'-fluoro-5'-O-tert-butyldiphenylsilyl-3'-deoxythymidine

3'-Fluoro-5'-O-trityl-deoxythymidine

5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine

5'-O-tert-butyldiphenylsilylthymidine

Downstream raw materials:

5-(2,2,2-trifluoroethoxy)methyl-3'-fluoro-5'-O-tert-butyldiphenylsilyl-2',3'-dideoxyuridine