1-[(2R,3S,5S)-3-fluoro-5-(trityloxymethyl)thiolan-2-yl]pyrimidine-2,4-dione | 165399-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[(2R,3S,5S)-3-fluoro-5-(trityloxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 165399-43-9
• 化学式: C₂₈H₂₅FN₂O₃S
• 分子量: 488.583
• InChiKey: FCXFTJQYZHXZCF-KYPHJKQUSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,5S)-3-fluoro-5-(trityloxymethyl)thiolan-2-yl]pyrimidine-2,4-dione 在 溶剂黄146 作用下， 以70%的产率得到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
• 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 、 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-(trityloxymethyl)thiolan-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

• The Stereochemical Outcome of the DAST Fluorination of 4′-Thiopyrimidine Nucleosides with “Up” Hydroxyl Groups is Controlled by the Oxidation State of the Sulfur Atom
  作者：Lak S. Jeong、Victor E. Marquez

  DOI：10.1246/cl.1995.301

  日期：1995.4

  DAST fluorination of 1-(5-O-trityl-3-deoxy-4-thio-β-d-threo-pentofuranosyl)uracil proceeds with retention of configuration, while the corresponding sulfoxide gives mainly the inverted product. The sulfone proceeds with elimination.

  1-(5-O-三苯甲基-3-脱氧-4-硫代-β-D-苏式-呋喃戊糖基)尿嘧啶的DAST氟化反应在保持构象不变的情况下进行，而相应的亚砜主要产生反式产物。砜则发生消除反应。
• 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