1-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione | 166812-87-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 166812-87-9
• 化学式: C₉H₁₁FN₂O₃S
• 分子量: 246.262
• InChiKey: LFUVOBMUXMAYFR-VMHSAVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 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：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione 生成 4-Amino-1-((2R,3S,5S)-3-fluoro-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Biological Activity of Sugar-Fluorinated 2',3'-dideoxy-4'-thioribofuranosyl Nucleosides

  摘要：

  DOI：

  10.1080/15257779508012426
• 作为产物：
  描述：

  (2R,4S,6S)-4-(trityloxymethyl)-7-oxa-3-thia-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one 在 sodium hydroxide 、 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 1-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups

  摘要：

  Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were confirmed by X-ray analysis.

  DOI：

  10.1016/s0040-4039(00)78345-6

文献信息

• Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups
  作者：Lak S. Jeong、Marc C. Nicklaus、Cliff George、Victor E. Marquez

  DOI：10.1016/s0040-4039(00)78345-6

  日期：1994.10

  Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were confirmed by X-ray analysis.
• Synthesis and Biological Activity of Sugar-Fluorinated 2',3'-dideoxy-4'-thioribofuranosyl Nucleosides
  作者：Victor Marquez、Lak Jeong、Marc Nicklaus、Cliff George

  DOI：10.1080/15257779508012426

  日期：1995.5.1