3-((4aR,6R,6aR,9aR,9bS)-8-Ethoxy-2,2-dimethyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-6-yl)-propionitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((4aR,6R,6aR,9aR,9bS)-8-Ethoxy-2,2-dimethyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-6-yl)-propionitrile
• 英文别名: 3-[(1S,2R,6R,7R,9R)-4-ethoxy-12,12-dimethyl-3,8,11,13-tetraoxatricyclo[7.4.0.02,6]tridecan-7-yl]propanenitrile
• 化学式: C₁₆H₂₅NO₅
• 分子量: 311.378
• InChiKey: NVGVVJJHNYRNMO-SGTIQLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,6-O-异亚丙基-D-葡萄糖醛 在 偶氮二异丁腈 溴 、 三正丁基氢锡 、 三乙胺 作用下， 以 苯 为溶剂， 反应 4.5h， 生成 3-((4aR,6R,6aR,9aR,9bS)-8-Ethoxy-2,2-dimethyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-6-yl)-propionitrile
  参考文献：
  名称：

  Serial radical reactions of enol ethers: ready routes to highly functionalized C-glycosyl derivatives

  摘要：

  DOI：

  10.1021/ja00191a064

文献信息

• Serial Radical Reactions of Glycals: Ready Routes to Highly Functionalized C-Glycosyl Derivatives
  作者：J. Cristobal Lopez、Ana M. Gomez、Bert Fraser-Reid

  DOI：10.1021/jo00117a044

  日期：1995.6

  The C3-OH of partially protected glycals can be readily converted into mixed acetals of 2-bromoacetaldehyde or into silylmethylene bromides. Reaction of these derivatives with tri-n-butyltin hydride gives a radical that cyclizes efficiently to generate a stabilized radical at C1. The latter can be trapped very efficiently with acrylonitrile, tert-butyl isocyanide, allyltri-n-butyltin, tributyltin acrylates, or a complex pyranoside enone to afford C-glycosides in which a 1,2 disubstitution has taken place. The stereochemistry of the resulting 1,2 disubstituted product is dependent, at C-2, on the stereochemistry of the C3-OH and at the anomeric center (C-1) upon the interplay of (a) steric effects and (b) the electronic bias of the radical anomeric effect.
• Serial radical reactions of enol ethers: ready routes to highly functionalized C-glycosyl derivatives
  作者：J. Cristobal Lopez、Bert Fraser-Reid

  DOI：10.1021/ja00191a064

  日期：1989.4