ethyl 5-[(2R,3S,4S)-4-azido-3-chlorooxolan-2-yl]-2-methylfuran-3-carboxylate | 945214-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-[(2R,3S,4S)-4-azido-3-chlorooxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 945214-48-2
• 化学式: C₁₂H₁₄ClN₃O₄
• 分子量: 299.714
• InChiKey: LUXISTVYYVEKLC-INTQDDNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-[(2R,3S,4S)-4-azido-3-chlorooxolan-2-yl]-2-methylfuran-3-carboxylate 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of furanosyl α-C-glycosides derived from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities

  摘要：

  Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl alpha-C-glycoside derivatives. The absolute configuration of 3-acetyl- 2-methyl-5-(2'-chloro-D-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.079
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 5-[(2R,3S,4S)-4-azido-3-chlorooxolan-2-yl]-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Synthesis of furanosyl α-C-glycosides derived from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities

  摘要：

  Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl alpha-C-glycoside derivatives. The absolute configuration of 3-acetyl- 2-methyl-5-(2'-chloro-D-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.079

文献信息

• Synthesis of furanosyl α-C-glycosides derived from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities
  作者：Lin Yan、Gui-Fu Dai、Jian-Li Yang、Feng-Wu Liu、Hong-Min Liu

  DOI：10.1016/j.bmcl.2007.03.079

  日期：2007.6

  Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl alpha-C-glycoside derivatives. The absolute configuration of 3-acetyl- 2-methyl-5-(2'-chloro-D-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated. (c) 2007 Elsevier Ltd. All rights reserved.