96829-18-4

Upstream product

• 58589-18-7 3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 
• 129580-08-1 3',5'-di-O-acetyl-5-(methoxymethyl)-2'-deoxyuridine 
• 76-83-5 trityl chloride 
• 5116-22-3 2'-deoxy-5-(methoxymethyl)uridine 

Downstream Products

• 125967-80-8 Methanesulfonic acid (2R,3S,5R)-5-(5-methoxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 104639-39-6 5-methoxymethyl-1-(2'-deoxy-β-D-lyxofuranosyl)uracil 
• 125967-79-5 1-((2R,4R,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methoxymethyl-1H-pyrimidine-2,4-dione 
• 308832-28-2 (1R,9R,10R)-4-Methoxymethyl-10-trityloxymethyl-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one 

Relevant academic research and scientific papers

Antiviral activity, antimetabolic activity and cytotoxicity of 3'-substituted deoxypyrimidine nucleosides

The antiviral activity, effect on cellular DNA and RNA synthesis, and cytotoxicity toward mammalian cells of 5-fluoro-2'-deoxyuridine, 5-methoxymethyl-2'-deoxyuridine, 2'-deoxythymidine, and their corresponding 3'-p-nitrophenylphosphate and 3'-p-aminophenylphosphate derivatives were determined. The 3'-p-aminophenylphosphate-2'-deoxy-5-methoxymethyluridine derivative was as potent as 5-methoxymethyl-2'-deoxyuridine in inhibiting herpes simplex viruses; however, 3'-p-aminophenylphosphate-2'-deoxy-5-fluorouridine was less potent than 5-fluoro-2'-deoxyuridine in inhibiting viral replication. The results suggest that the deoxypyrimidine ribonucleoside kinase has bulk tolerance for substituents at the 3-position of the ribofuranose moiety. The effect on cellular DNA and RNA synthesis and cytotoxicity toward mammalian cells were monitored by studying the incorporation of radioactive precursors. 5-Methoxymethyl-2'-deoxyuridine and 3'-p-aminophenylphosphate-2'-deoxy-5-methoxymethyluridine failed to inhibit DNA or RNA synthesis. 5-Fluoro-2'-deoxyuridine and 3'-p-aminophenylphosphate-2'-deoxy-5-fluorouridine decreased incorporation of [3H]deoxyuridine by 50% at 1.0 and 40 μM, respectively. Cytotoxicity (microscopic lesions using monolayer cells) on exposure to 5-methoxymethyl-2'-deoxyuridine, 3'-p-aminophenylphosphate-2'-deoxy-5-methoxymethyluridine, 5-fluoro-2'-deoxyuridine, and 3'-p-aminophenylphosphate-2'-deoxy-5-fluorouridine was observed at 3800, 1600, 1.6, and 110 μM, respectively.

A facile one-pot synthesis of 2,3'-anhydro-2'-deoxyuridines via 3'-O-imidazolylsulfonates

Continued interests in the novel synthetic methods of the pivotal compound, 2,3'-anhydro-2'-deoxyribonucleosides (7) uncovered a facile one-pot conversion of 5 with 1,1'-sulfonyldiimidazole in basic conditions to 7 with almost quantitative yields (91-99%).