methyl (2S,3S,5R,6E)-9-benzoyloxy-3-hydroxy-2,5-oxy-6-nonenoate | 1042909-06-7

• 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,6E)-9-benzoyloxy-3-hydroxy-2,5-oxy-6-nonenoate
• 英文别名: methyl (2S,3S,5R)-5-[(E)-4-benzoyloxybut-1-enyl]-3-hydroxyoxolane-2-carboxylate
• CAS: 1042909-06-7
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: HZBUTAKQZZEMEN-YBBQVAIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,5R,6E)-9-benzoyloxy-3-hydroxy-2,5-oxy-6-nonenoate 、 乙酸酐 在 4-二甲氨基吡啶 、 TEA 作用下， 生成 methyl (2S,3S,5R,6E)-3-acetoxy-9-benzoyloxy-2,5-oxy-6-nonenoate
  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：

  methyl (2S,3S,5S,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate 在 CuCl₂*2H₂O 作用下， 以 乙腈 为溶剂， 以76%的产率得到methyl (2S,3S,5S,6Z)-5-acetoxy-9-benzoyloxy-2,3-dihydroxy-6-nonenoate
  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

文献信息

• Stereoselective Synthesis of 3-Oxygenated-<i>cis</i>-dialkyl-2,5-substituted Tetrahydrofurans from Cyclohexadienediols
  作者：Margarita Brovetto、Gustavo Seoane

  DOI：10.1021/jo800514k

  日期：2008.8.1

  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.