5-bromo-2’,3’,5’-tri-O-acetyluridine

Base Information

• Chemical Name: 5-bromo-2’,3’,5’-tri-O-acetyluridine
• CAS No.: 105659-31-2
• Molecular Formula: C₁₅H₁₇BrN₂O₉
• Molecular Weight: 449.212
• Mol file: 105659-31-2.mol

Synonyms:

Chemical Property of 5-bromo-2’,3’,5’-tri-O-acetyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-bromo-2’,3’,5’-tri-O-acetyluridine

There total 7 articles about 5-bromo-2’,3’,5’-tri-O-acetyluridine 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: 98.0%

Tri-O-acetyluridine (4105-38-8) → 5-bromo-2’,3’,5’-tri-O-acetyluridine (105659-31-2,105659-32-3)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 40 ℃; for 2h;

DOI:10.1016/j.tetlet.2012.04.081

Reference yield: 95.9%

5-bromouridine (957-75-5) + acetic anhydride (108-24-7) → 5-bromo-2’,3’,5’-tri-O-acetyluridine (105659-31-2,105659-32-3)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1002/anie.201001242

Reference yield: 93.0%

2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine (33282-64-3) + 1,2,3,5-tetraacetylribose (13035-61-5) → 5-bromo-2’,3’,5’-tri-O-acetyluridine (105659-31-2,105659-32-3)

Guidance literature:

With poly(4,5-diphenyl-2-vinyloxazolium perchlorate); In acetonitrile; for 6h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2017.03.046

upstream raw materials:

Tri-O-acetyluridine

5-bromouridine

acetic anhydride

5-bromouracil

Downstream raw materials:

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

5-bromouridine

5-bromo-N3-benzoyl-2’,3’,5’-tri-O-acetyluridine

N₃-benzoyl-2',3',5'-O-triacetoxyuridine-5-malonic acid dimethyl ester