Acetic acid (2R,3S,5R)-5-(4-methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester | 210910-68-2

• 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: Acetic acid (2R,3S,5R)-5-(4-methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS: 210910-68-2
• 化学式: C₂₀H₂₄N₂O₈S
• 分子量: 452.485
• InChiKey: RDCAZKFEGCUIND-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123.02
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-5-(4-methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester 在 potassium fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Rapid synthesis of a 5′-fluorinated oligodeoxy-nucleotide: A model antisense probe for use in imaging with positron emission tomography (PET)

  摘要：

  5'-Deoxy-5'-fluoro-O-4-methylthymidine was synthesized by the reaction of the corresponding 5'-O-tosylate with KF in the presence of Kryptofix [222] and coupled to a 5'-phosphoramidite-activated CPG-bound oligodeoxynucleotide. The sequence of reactions and purifications were accomplished within 4 h, a necessary condition of the development of radiofluorinated antisense oligodeoxynucleotide, probe for use with PET. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00239-x
• 作为产物：
  描述：

  4-O-甲基-胸苷 在 吡啶 作用下， 生成 Acetic acid (2R,3S,5R)-5-(4-methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Rapid synthesis of a 5′-fluorinated oligodeoxy-nucleotide: A model antisense probe for use in imaging with positron emission tomography (PET)

  摘要：

  5'-Deoxy-5'-fluoro-O-4-methylthymidine was synthesized by the reaction of the corresponding 5'-O-tosylate with KF in the presence of Kryptofix [222] and coupled to a 5'-phosphoramidite-activated CPG-bound oligodeoxynucleotide. The sequence of reactions and purifications were accomplished within 4 h, a necessary condition of the development of radiofluorinated antisense oligodeoxynucleotide, probe for use with PET. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00239-x