Acetic acid (2S,3R,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-fluoro-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 725260-78-6

• 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 (2S,3R,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-fluoro-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 725260-78-6
• 化学式: C₁₅H₁₇FN₂O₈S
• 分子量: 404.373
• InChiKey: KPMUXVKAIMMURA-SFTQSGBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-fluoro-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以63%的产率得到1-(β-L-lyxofuranosyl)-5-fluorocytosine
  参考文献：
  名称：

  Stereospecific synthesis and biological evaluations of β-l-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

  摘要：

  In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta -L-nucleoside analogues. In this paper, we report on the synthesis Of beta -L-pentofuranonucleosides (and their 2 ' -deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01238-7
• 作为产物：
  描述：

  1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil 在 劳森试剂 、 吡啶 、 氨 、 水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 Acetic acid (2S,3R,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-fluoro-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Stereospecific synthesis and biological evaluations of β-l-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

  摘要：

  In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta -L-nucleoside analogues. In this paper, we report on the synthesis Of beta -L-pentofuranonucleosides (and their 2 ' -deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01238-7