β-L-FddClU

• 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: β-L-FddClU
• 英文别名: 5-chloro-2',3'-dideoxy-3'-fluoro-β-L-uridine；5-chloro-1-[(2S,4R,5S)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione；5-chloro-1-[(2S,4R,5S)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₉H₁₀ClFN₂O₄
• 分子量: 264.641
• InChiKey: WKVDSZYIGHLONN-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基 2-脱氧-L-苏式-呋喃戊糖苷 在 吡啶 、 三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 61.5h， 生成 β-L-FddClU
  参考文献：
  名称：

  Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol

  摘要：

  2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00312-2

文献信息

• Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol
  作者：Byoung K Chun、Raymond F Schinazi、Yung-Chi Cheng、Chung K Chu

  DOI：10.1016/s0008-6215(99)00312-2

  日期：2000.8

  2',3'-Dideoxy-3'-fluoro-L-ribonucleosides were synthesized as potential antiviral agents. The key intermediate, methyl 5-O-benzoyl-2,3-dideoxy-3-fluoro-L-ribofuranoside, which was prepared from D-sorbitol, was condensed with pyrimidine and purine bases to obtain the respective nucleosides. Among them, the cytosine analogue 2',3'-dideoxy-3'-fluoro-alpha-L-cytidine showed a moderate anti-HBV activity. (C) 2000 Elsevier Science Ltd. All rights reserved.