1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione | 1335224-06-0

• 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: 1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1335224-06-0
• 化学式: C₁₈H₂₀N₂O₇
• 分子量: 376.366
• InChiKey: YWOGIANJHZFDLD-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 以 甲醇 、 水 为溶剂， 以100%的产率得到beta-胸苷
  参考文献：
  名称：

  Photolabile thymidine cleavable with a 532 nanometer laser

  摘要：

  The synthesis and characterization of a novel 3' p-hydroxyphenacyl-caged thymidine bearing a 5' N,N-diisopropylcyanoethylphosphoramidite is presented representing a new methodology for the photoregulation of PCR and gene expression. Solid phase oligonucleotide synthesis affords a primer blocked at the 3' position, which could function as a phototrigger for polymerase activity. The caging group exhibits quantitative photolysis in 15 s using a 532 nm green hand laser. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.052
• 作为产物：
  描述：

  保护胸苷 在 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.75h， 生成 1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(4-hydroxyphenyl)-2-oxoethoxy]tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Photolabile thymidine cleavable with a 532 nanometer laser

  摘要：

  The synthesis and characterization of a novel 3' p-hydroxyphenacyl-caged thymidine bearing a 5' N,N-diisopropylcyanoethylphosphoramidite is presented representing a new methodology for the photoregulation of PCR and gene expression. Solid phase oligonucleotide synthesis affords a primer blocked at the 3' position, which could function as a phototrigger for polymerase activity. The caging group exhibits quantitative photolysis in 15 s using a 532 nm green hand laser. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.052