5-fluoro-1-(cis-3'-fluoro-2',3',4',5'-tetrahydro-2'-furanyl)uracil | 130410-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-fluoro-1-(cis-3'-fluoro-2',3',4',5'-tetrahydro-2'-furanyl)uracil
• 英文别名: (+/-)-5-fluoro-1-((2'R,3'S)-3'-fluorotetrahydrofuran-2'-yl)pyrimidine-2,4(1H,3H)-dione；5-fluoro-1-[(2R,3S)-3-fluorooxolan-2-yl]pyrimidine-2,4-dione
• CAS: 130410-01-4；130433-81-7
• 化学式: C₈H₈F₂N₂O₃
• 分子量: 218.16
• InChiKey: MXCUBMDGIBAUAE-MHTLYPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-Fluorooxolan-2-ol 、 2,4-O-bis(trimethylsilyl)-5-fluorouracil 在 二甲基溴化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 以22%的产率得到5-fluoro-1-(cis-3'-fluoro-2',3',4',5'-tetrahydro-2'-furanyl)uracil
  参考文献：
  名称：

  Synthesis of 1′,2′-cis-Nucleoside Analogues: Evidence of Stereoelectronic Control for S_N2 Reactions at the Anomeric Center of Furanosides

  摘要：

  We are reporting a highly diastereoselective route to 1 ',2 '-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.

  DOI：

  10.1021/ja104429y

文献信息

• Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system
  作者：Teruo Umemoto、Shinji Fukami、Ginjiro Tomizawa、Kikuko Harasawa、Kosuke Kawada、Kyoichi Tomita

  DOI：10.1021/ja00179a047

  日期：1990.11

  N-Fluoropyridinium salts provide a new system of fluorinating agents by which a wide range of nucleophilic substrates differing in reactivity can be fluorinated due to the varying degree of fluorinating power and also fluorinated very selectively through structural alteration. The scope of selective fluorination should be broadened considerably on the basis of the present results. The N-fluoropyridinium

  N-氟吡啶鎓盐提供了一种新的氟化剂系统，通过该系统，由于氟化能力的不同程度，反应性不同的各种亲核底物可以被氟化，并且还可以通过结构改变非常有选择性地氟化。在现有结果的基础上，选择性氟化的范围应该大大拓宽。因此，N-氟吡啶鎓盐系统应该可以制备许多有用的有机氟化合物
• UMEMOTO, TERUO;FUKAMI, SHINJI;TOMAZAWA, GINJIRO;HARASAWA, KIKUKA;KAWADA, +, J. AMER. CHEM. SOC., 112,(1990) N3, C. 8563-8575
  作者：UMEMOTO, TERUO、FUKAMI, SHINJI、TOMAZAWA, GINJIRO、HARASAWA, KIKUKA、KAWADA, +

  DOI：——

  日期：——