18814-21-6

Basic information

• Product Name: 5-FLUOROURIDINE
• Synonyms: Nsc258350
• CAS NO: 18814-21-6
• Molecular Formula: C₉H₁₁FN₂O₆
• Molecular Weight: 0
• Mol File: 18814-21-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.77g/cm³
• CAS DataBase Reference: 5-FLUOROURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUOROURIDINE(18814-21-6)
• EPA Substance Registry System: 5-FLUOROURIDINE(18814-21-6)

Safety Data

• Hazardous Substances Data: 18814-21-6(Hazardous Substances Data)

Upstream product

• 51-21-8 5-fluorouracil 
• 58-96-8 uridine 
• 77180-90-6 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-fluorouracil 
• 58-96-8 L-uridine 
• 1748-04-5 (2S,3S,4S,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 390824-25-6 1,5-di-O-acetyl-3-O-benzyl-2-O-methanesulfonyl-L-arabinofuranose 
• 390824-27-8 methyl 2,5-di-O-acetyl-3-O-benzyl-β-L-ribofuranoside 
• 390824-31-4 1-(2',5'-di-O-acetyl-3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil 
• 390824-28-9 1,2,5-tri-O-acetyl-3-O-benzyl-β-L-ribofuranose 
• 390824-26-7 methyl 3-O-benzyl-β-L-ribofuranoside 
• 173009-66-0 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-ribofuranose 
• 171721-12-3 1,2-di-O-isopropylidene-3,5-di-O-benzoyl-α-L-ribofuranose 
• 849342-81-0 C₂₅H₂₁FN₂O₉ 
• 446251-78-1 1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil 

Relevant articles and documents

THERMOSTABLE BIOCATALYST COMBINATION FOR NUCLEOSIDE SYNTHESIS

The present invention relates to a transglycosylation method for the preparation of natural and synthetic nucleosides using a uridine phosphorylase (PyNPase, E.C. 2.4.2.3), a purine nucleoside phosphorylase (PNPase, E.C. 2.4.2.1), or a combination thereof. These biocatalysts may be used as such, or by means of host cells transformed with vectors comprising recombinant DNA gene derived from hyperthermophilic archaea and encoding for the PyNPase and PNPase enzymes.

A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular SN2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbrüggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.

Stereospecific synthesis and biological evaluations of β-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural β-L-nucleoside analogues. In this paper, we report on the synthesis of β-L-pentofuranonucleosides (and their 2′-deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated.