3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine | 291525-18-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine
• 英文别名: 5-[(2-benzyl-1,3-dithian-2-yl)methyl]-1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 291525-18-3
• 化学式: C₃₃H₅₄N₂O₅S₂Si₂
• 分子量: 679.105
• InChiKey: TWBKIWNCRZJVMO-UPRLRBBYSA-N

物化性质

• 熔点：
  83-85 °C
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine 在 氢氟酸 、 三乙胺 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 5-(1-(3-phenyl-2-oxopropyl))-2'-deoxyuridine
  参考文献：
  名称：

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

  摘要：

  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, k(Trap) = 46.1 +/- 15.4 M-1 s(-1); propan-2-ol, k(Trap) = 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.

  DOI：

  10.1021/jo000271s
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 环己烷 为溶剂， 反应 25.0h， 生成 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine
  参考文献：
  名称：

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

  摘要：

  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, k(Trap) = 46.1 +/- 15.4 M-1 s(-1); propan-2-ol, k(Trap) = 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.

  DOI：

  10.1021/jo000271s

文献信息

• Independent Generation and Reactivity of 2‘-Deoxy-5-methyleneuridin-5-yl, a Significant Reactive Intermediate Produced from Thymidine as a Result of Oxidative Stress
  作者：Aaron S. Anderson、Jae-Taeg Hwang、Marc M. Greenberg

  DOI：10.1021/jo000271s

  日期：2000.7.1

  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, k(Trap) = 46.1 +/- 15.4 M-1 s(-1); propan-2-ol, k(Trap) = 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.