methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate | 1042909-00-1

• 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)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate
• 英文别名: methyl (4S,5S)-5-[(2R)-2-acetyloxy-3-oxopropyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 1042909-00-1
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: OPKKNRZNZGFJCZ-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲醇 、 (1S,2S,5R)-3-chloro-1,2-isopropylidenedioxycyclohex-3-en-5-yl acetate 在 碳酸氢钠 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate
  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