1-(α-L-Lyxofuranosyl)-5-fluorocytosine | 1382683-43-3

• 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: 1-(α-L-Lyxofuranosyl)-5-fluorocytosine
• 英文别名: 4-amino-1-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one
• CAS: 1382683-43-3
• 化学式: C₉H₁₂FN₃O₅
• 分子量: 261.21
• InChiKey: STRZQWQNZQMHQR-LENIQADQSA-N

物化性质

• 沸点：
  511.4±60.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 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：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(α-L-Lyxofuranosyl)-5-fluorocytosine 在 咪唑 、 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine
  参考文献：
  名称：

  Total Synthesis of α-Elvucitabine

  摘要：

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.

  DOI：

  10.1080/00397911.2011.571805
• 作为产物：
  描述：

  methyl L-lyxofuranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 1-(α-L-Lyxofuranosyl)-5-fluorocytosine
  参考文献：
  名称：

  Total Synthesis of α-Elvucitabine

  摘要：

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.

  DOI：

  10.1080/00397911.2011.571805

文献信息

• Total Synthesis of α-Elvucitabine
  作者：Guilong Zhao、Yuanyuan Lou、Linshan Zhang、Hua Shao、Weiren Xu、Lida Tang、Meixiang Zou

  DOI：10.1080/00397911.2011.571805

  日期：2012.10

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.