(2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine

Base Information

• Chemical Name: (2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine
• CAS No.: 95740-26-4
• Molecular Formula: C11H11FN2O5
• Molecular Weight: 270.2138
• Mol file: 95740-26-4.mol

Synonyms:(2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine;(2’S)-2’-DEOXY-2’-FLUORO-5-ETHYNYLURIDINE;

Chemical Property of (2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 104.55000
• Density: 1.6g/cm³
• LogP: -1.89340

Purity/Quality:

97% ^*data from raw suppliers

(2’S)-2’-Deoxy-2’-fluoro-5-ethynyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine is a commonly used probe for DNA synthesis in vivo as it exhibits minimal impact on genome function in diverse tissue types. (2′S)-2′-deoxy-2′-fluoro-5-ethynyluridine is also ideally suited for metabolic DNA labeling when prolonged cell survival and undisturbed cell cycle progression are necessary, such as for pulse-chase experiments aimed at “birth dating” DNA in vivo. A probe for DNA synthesis in vivo that is less toxic than both EdU and BrdU. Ideally suited for metabolic DNA labeling when prolonged cell survival and undisturbed cell cycle progression are required.

Technology Process of (2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine

There total 4 articles about (2'S)-2'-Deoxy-2'-fluoro-5-ethynyluridine 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: 69.0%

5-(2-trimethylsilylethynyl)-2′-deoxy-2′-fluoro-3′,5′-di-O-benzoyl-D-arabinouridine → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyluracil (95740-26-4)

Guidance literature:

5-(2-trimethylsilylethynyl)-2′-deoxy-2′-fluoro-3′,5′-di-O-benzoyl-D-arabinouridine; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1039/c9ob01515a

Reference yield: 62.0%

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-<2-(trimethylsilyl)ethynyl>uracil (95740-25-3) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyluracil (95740-26-4)

Guidance literature:

With sodium hydroxide; In methanol; for 5h; Ambient temperature;

DOI:10.1021/jm00383a009

Reference yield:

1-((2R,3S,4R,5R)-3-Fluoro-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-trimethylsilanylethynyl-1H-pyrimidine-2,4-dione (95740-23-1) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyluracil (95740-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O / dimethylsulfoxide / 2 h / Ambient temperature

2: 62 percent / NaOH / methanol / 5 h / Ambient temperature

With sodium hydroxide; water; In methanol; dimethyl sulfoxide;

DOI:10.1021/jm00383a009

upstream raw materials:

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-<2-(trimethylsilyl)ethynyl>uracil

1-((2R,3S,4R,5R)-3-Fluoro-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-trimethylsilanylethynyl-1H-pyrimidine-2,4-dione

fialuridine

Refernces

• 1、 Perlman,Watanabe,Schinazi,Fox. "Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro- β-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents". . p. 741 - 748. Retrieved 2007/10/02.