1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 170638-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 170638-74-1
• 化学式: C₁₇H₂₈N₂O₄Si
• 分子量: 352.506
• InChiKey: DRMLYFORIRCFDZ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 三乙基硼氢化锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.33h， 生成 3'-C-methylthymidine
  参考文献：
  名称：

  Pfundheller, Henrik M.; Jorgensen, Pia N.; Sorensen, Ulrik S., Journal of the Chemical Society. Perkin transactions I, 1998, # 8, p. 1409 - 1421

  摘要：

  DOI：
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 重铬酸吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Novel 3′-C-(Hydroxymethyl)thymidines and Oligodeoxynucleotide Analogues Containing Compressed 3′-C-Hydroxymethyl-Linked Phosphodiester Backbones

  摘要：

  Lombardo methylenation of the novel 2'-deoxy-3'-ketonucleosides 4 afforded 2',3'-dideoxy-3'-C-methylene nucleosides 5, which were subjected to catalytic dihydroxylation reactions. In the case of 5'-deoxynucleoside 5a, a 1:1 mixture of 3'-C-hydroxymethyl diastereoisomers 6a and 7a was obtained, whereas the 5'-O-silylated nucleoside 5b afforded 3'-C-(hydroxymethyl)thymidine derivative 6b as the only product. Sharpless asymmetric dihydroxylation of 5a proceeded in low yield to give 5a and 7a as a 10:3 mixture. 5'-O-Silylated nucleoside 6b was converted into the phosphoramidite synthon 9, which was applied in automated syntheses of oligodeoxynucleotides containing novel compressed 3'-C-hydroxymethyl-linked phosphodiester backbones.

  DOI：

  10.1080/15257779508009485

文献信息

• Synthesis of C3′ Modified Nucleosides for Selective Generation of the C3′-Deoxy-3′-thymidinyl Radical: A Proposed Intermediate in LEE Induced DNA Damage
  作者：Suaad A. S. Audat、CherylAnn Trzasko Love、Buthina A. S. Al-Oudat、Amanda C. Bryant-Friedrich

  DOI：10.1021/jo300045m

  日期：2012.4.20

  3′-dideoxy-C3′-thymidinyl radical (C3′dephos sugar radical), phenyl selenide and acyl modified sugar and nucleoside derivatives have been synthesized, and their suitability as photochemical precursors of the radical of interest has been evaluated. Upon photochemical activation of C3′-derivatized nucleosides in the presence of the hydrogen atom donor tributyltin hydride, 2′,3′-dideoxythymidine is formed

  据信由低能电子（LEE）诱导的DNA损伤途径涉及2-脱氧核糖自由基的形成。这些自由基形成在核苷酸的C3'和C5'位置，是通过将LEEs从核碱基转移至DNA寡聚体的磷酸基团而裂解C–O磷酸二酯键的结果。已经获得了大量信息，以阐明通过该过程形成的未修饰寡核苷酸产物的身份。然而，关于由这些糖基的降解形成的修饰病变的性质的信息很少。确定通过2'，3'-二脱氧-C3'-胸苷基（C3'dephos糖自由基），苯基硒化物和酰基修饰的糖以及核苷衍生物已经合成，并且已经评估了它们作为目标自由基的光化学前体的适用性。在存在氢原子供体三丁基锡氢化物的情况下，对C3'衍生的核苷进行光化学活化后，形成2'，3'-二脱氧胸苷，表明选择性生成了C3'磷酸基团。这些前体将使鉴定和量化由LEEs产生的自由基引起的DNA损伤的产物成为可能。
• 3'-C-Hydroxymethylthymidine: Synthesis and Incorporation into Oligodeoxynucleotide Analogues
  作者：Pia Nøncgaard Jørgensen、Margit Svendsen、Claus Nielsen、Jesper Wengel

  DOI：10.1080/15257779508012502

  日期：1995.5.1

  The stereoselective synthesis of 3'-C-hydroxymethylthymidine (5) in five steps from thymidine has been accomplished and this nucleoside has been incorporated into oligodeoxynucleotides (ODNs) in different ways.