3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE

Base Information

• Chemical Name: 3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE
• CAS No.: 110522-47-9
• Molecular Formula: C₁₃H₁₅FN₂O₇
• Molecular Weight: 330.27
• Mol file: 110522-47-9.mol

Synonyms:3’,5’-DI-O-ACETYL-5-FLUORO-2’-DEOXYURIDINE;3’,5’-DI-O-ACETYL-5-FLUORO-2’-DEOXY-D-URIDINE;3’,5’-Di-O-acetyl-2’-deoxy-5-fluoro-D-uridine

Chemical Property of 3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE

Chemical Property:

• PKA: 7.63±0.10(Predicted)
• PSA: 116.69000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: -0.54200

Purity/Quality:

98%Min ^*data from raw suppliers

3’,5’-Di-O-acetyl-5-fluoro-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3’,5’-Di-O-acetyl-5-fluoro-2’-deoxyuridine is a derivative of 2’-Fluoro-2’-deoxyuridine (F590275), which is a component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer.

Technology Process of 3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE

There total 8 articles about 3',5'-DI-O-ACETYL-5-FLUORO-2'-DEOXYURIDINE 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: 97.0%

acetic anhydride (108-24-7) + 5-Fluoro-2'-deoxyuridine (50-91-9) → 1-(2'-deoxy-3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil (110522-47-9,7207-56-9)

Guidance literature:

With pyridine; at 20 ℃; for 8h;

DOI:10.1016/j.bmc.2011.04.015

Reference yield: 74.7%

3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1) → 1-(2'-deoxy-3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil (110522-47-9,7207-56-9)

Guidance literature:

With 4 A molecular sieve; fluorine; In ethanol; chloroform; trichlorofluoromethane; at -78 ℃;

DOI:10.1016/0022-1139(94)03070-7

Reference yield: 25.7%

vinyl acetate (108-05-4,9003-20-7) + 5-Fluoro-2'-deoxyuridine (50-91-9) → 5'-O-acetyl-floxuridine (2823-52-1) + Acetic acid (2R,3S)-2-acetoxymethyl-5-((S)-5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (7207-56-9,110522-47-9) + 3′-O-acetyl-5-fluoro-2′-deoxyuridine (2059-38-3)

Guidance literature:

PS (Pseudomonas sp. lipase); In 1,4-dioxane;

DOI:10.1016/S0040-4039(00)88556-1

upstream raw materials:

Acetic acid (2R,3S)-2-acetoxymethyl-5-fluoro-tetrahydro-furan-3-yl ester

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

acetic anhydride

5-Fluoro-2'-deoxyuridine

Downstream raw materials:

1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-fluoro-4-octadecylamino-1H-pyrimidin-2-one

5-Fluoro-2'-deoxyuridine

3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine

2'-deoxy-3',5'-di-O-acetyl-3-(2,3-dimethoxybenzoyl)-5-fluorouridine

Refernces

• 1、 Coe, Paul L.,Talekar, Ratnakar R.,Walker, Richard T.. "The synthesis of difluoro and trifluoro analogues of pyrimidine deoxyribonucleosides: a novel approach using elemental fluorine". . p. 19 - 24. Retrieved 1994.
• 2、 Zhang, Xiaohui,Wang, Jian,Xu, Yao-Zhong. "Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides". . p. 523 - 529. Retrieved 2013/09/02.