622379-83-3

Usage

Class

Azauridines

Type of compound

Modified nucleoside

Potential activities

Antiviral and antitumor

Viruses targeted

Herpes simplex virus and respiratory syncytial virus

Anti-cancer properties

Shows promise in inhibiting the growth of tumor cells

Potential use

Therapeutic agent for the treatment of viral infections and cancer

Additional research needed

To fully understand its mechanisms of action and potential applications.

Upstream product

• 461-89-2 6-azauracil 
• 15397-15-6 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 98-88-4 benzoyl chloride 
• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 

Downstream Products

• 622379-88-8 2-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-5-thioxo-4,5-dihydro-2H-[1,2,4]triazin-3-one 

Relevant academic research and scientific papers

NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION

Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

2′-C-alkylribonucleosides: Design, synthesis, and conformation

Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.