(2R,3R)-4-[(3aR,9bS)-3,3-dimethyl-4,9b-dihydro-3aH-chromeno[4,3-c][1,2]oxazol-1-yl]-2,3-dibenzoyloxy-4-oxobutanoic acid | 169105-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-4-[(3aR,9bS)-3,3-dimethyl-4,9b-dihydro-3aH-chromeno[4,3-c][1,2]oxazol-1-yl]-2,3-dibenzoyloxy-4-oxobutanoic acid
• CAS: 169105-71-9
• 化学式: C₃₀H₂₇NO₉
• 分子量: 545.546
• InChiKey: QLYXGGOCLDPOQG-KVZCNWPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-[(3aR,9bS)-3,3-dimethyl-4,9b-dihydro-3aH-chromeno[4,3-c][1,2]oxazol-1-yl]-2,3-dibenzoyloxy-4-oxobutanoic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以98%的产率得到1,3a-4,9a-tetrahydro-3,3-dimethyl-cis-3H-<1>benzopyrano<4,3-c>isoxazole
  参考文献：
  名称：

  Highly efficient resolution of benzopyrano[4,3-c]isoxazolidine derivatives: Versatile chiral auxiliaries for asymmetric alkylation

  摘要：

  Benzopyrano[4,3-c]isoxazolidine derivatives, newly developed chiral auxiliaries for asymmetric alkylation, were synthesized and resolved in a unique manner. Resolution could be executed so efficiently that both enantiomers were obtained with a single resolving reagent in excellent yields.

  DOI：

  10.1016/0957-4166(95)00162-i
• 作为产物：
  描述：

  (3aS,9bR)-3,3-Dimethyl-1-(tetrahydro-pyran-2-yl)-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole 在 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (2R,3R)-4-[(3aR,9bS)-3,3-dimethyl-4,9b-dihydro-3aH-chromeno[4,3-c][1,2]oxazol-1-yl]-2,3-dibenzoyloxy-4-oxobutanoic acid
  参考文献：
  名称：

  Highly efficient resolution of benzopyrano[4,3-c]isoxazolidine derivatives: Versatile chiral auxiliaries for asymmetric alkylation

  摘要：

  Benzopyrano[4,3-c]isoxazolidine derivatives, newly developed chiral auxiliaries for asymmetric alkylation, were synthesized and resolved in a unique manner. Resolution could be executed so efficiently that both enantiomers were obtained with a single resolving reagent in excellent yields.

  DOI：

  10.1016/0957-4166(95)00162-i

文献信息

• Highly efficient resolution of benzopyrano[4,3-c]isoxazolidine derivatives: Versatile chiral auxiliaries for asymmetric alkylation
  作者：Atsushi Abiko、William M. Davis、Satoru Masamune

  DOI：10.1016/0957-4166(95)00162-i

  日期：1995.6

  Benzopyrano[4,3-c]isoxazolidine derivatives, newly developed chiral auxiliaries for asymmetric alkylation, were synthesized and resolved in a unique manner. Resolution could be executed so efficiently that both enantiomers were obtained with a single resolving reagent in excellent yields.