3',5'-bis-O-(tert-butyldimethylsilyl)-5-(1-(3-phenyl-2-hydroxypropyl))-2'-deoxyuridine | 291525-23-0

• 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-(1-(3-phenyl-2-hydroxypropyl))-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-(2-hydroxy-3-phenylpropyl)pyrimidine-2,4-dione
• CAS: 291525-23-0
• 化学式: C₃₀H₅₀N₂O₆Si₂
• 分子量: 590.908
• InChiKey: RJYDDWSXQVOSFD-ZIIKXKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-5-(1-(3-phenyl-2-hydroxypropyl))-2'-deoxyuridine 在 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到5-(1-(3-phenyl-2-hydroxypropyl))-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 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 calcium carbonate 、 mercury dichloride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 环己烷 、 水 、 乙腈 为溶剂， 反应 45.0h， 生成 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(1-(3-phenyl-2-hydroxypropyl))-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.