291525-18-3

Upstream product

• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 122-78-1 phenylacetaldehyde 
• 31593-52-9 2-benzyl-1,3-dithiane 
• 291525-17-2 3′,5′-bis-O-(tert-butyldimethylsilyl)-5-bromomethyl-2'-deoxyuridine 

Downstream Products

• 291525-23-0 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(1-(3-phenyl-2-hydroxypropyl))-2'-deoxyuridine 
• 291525-16-1 5-(1-(3-phenyl-2-oxopropyl))-2'-deoxyuridine 
• 73847-52-6 5-(2-phenylethyl)-2'-deoxyuridine 
• 291525-19-4 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2-oxopropyl)-2'-deoxyuridine 

Relevant academic research and scientific papers

Independent Generation and Reactivity of 2′-Deoxy-5-methyleneuridin-5-yl, a Significant Reactive Intermediate Produced from Thymidine as a Result of Oxidative Stress

2′-Deoxy-5-methyleneuridin-5-yl (1) is produced in a variety of DNA damage processes and is believed to result in the formation of lesions that are mutagenic and refractory to enzymatic repair. 2′-Deoxy-5-methyleneuridin-5-yl (1) was independently generated under anaerobic conditions via Norrish Type I photocleavage during Pyrex filtered photolysis of the benzyl ketone 7. The radical (1) exhibits behavior consistent with that of a resonance-stabilized radical. The KIE for hydrogen atom transfer from t-BuSH was found to be 7.3 ± 1.7. Competition studies between radical recombination and hydrogen atom donors (2,5-dimethyltetrahydrofuran, kTrap = 46.1 ± 15.4 M-1 s-1; propan-2-ol, kTrap = 13.6 ± 3.5 M-1 s-1) chosen to mimic the carbohydrate components of 2′-deoxyribonucleotides suggest that 2′-deoxy-5-methyleneuridin-5-yl (1) may be able to transfer damage from the nucleobase to the deoxyribose of an adjacent nucleotide in DNA under hypoxic conditions.