ethyl (Z)-3-[(1S,2R,6R,7R,9R)-4-ethoxy-12,12-dimethyl-3,8,11,13-tetraoxatricyclo[7.4.0.02,6]tridecan-7-yl]prop-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (Z)-3-[(1S,2R,6R,7R,9R)-4-ethoxy-12,12-dimethyl-3,8,11,13-tetraoxatricyclo[7.4.0.02,6]tridecan-7-yl]prop-2-enoate
• 化学式: C₁₈H₂₈O₇
• 分子量: 356.416
• InChiKey: CRHBNTBBSOAQCL-VIKGDMKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,6-Di-O-isopropylidene-3-O-(2-bromo-1-ethoxyethyl)-D-glucal 、 乙基(2E)-3-(三丁基锡烷基)丙烯酸酯 在 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以63%的产率得到ethyl (E)-3-[(1S,2R,6R,7R,9R)-4-ethoxy-12,12-dimethyl-3,8,11,13-tetraoxatricyclo[7.4.0.02,6]tridecan-7-yl]prop-2-enoate
  参考文献：
  名称：

  Serial Radical Reactions of Glycals: Ready Routes to Highly Functionalized C-Glycosyl Derivatives

  摘要：

  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.

  DOI：

  10.1021/jo00117a044