methyl (2S,3S,5R,6Z)-5-acetoxy-8-(1,3-dioxolan-2-yl)-2,3-isopropylidenedioxy-6-octenoate | 1042909-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,5R,6Z)-5-acetoxy-8-(1,3-dioxolan-2-yl)-2,3-isopropylidenedioxy-6-octenoate
• CAS: 1042909-02-3
• 化学式: C₁₇H₂₆O₈
• 分子量: 358.389
• InChiKey: MYKSNVAVLBSUIZ-GFPUUDHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate 、 2-(1,3-二氧戊环-2-基)乙基三苯基溴化磷 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以54%的产率得到methyl (2S,3S,5R,6Z)-5-acetoxy-8-(1,3-dioxolan-2-yl)-2,3-isopropylidenedioxy-6-octenoate
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Oxygenated-cis-dialkyl-2,5-substituted Tetrahydrofurans from Cyclohexadienediols

  摘要：

  The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures.

  DOI：

  10.1021/jo800514k