(3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone | 177607-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone
• 英文别名: (4R)-4-benzyl-3-[(2S,4S)-2,4-dimethyloctanoyl]-1,3-oxazolidin-2-one
• CAS: 177607-84-0
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: GVYYTODDSJNMLG-XYJFISCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以93%的产率得到(2S,4S)-2,4-dimethyloctanoic acid
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l
• 作为产物：
  描述：

  (2S)-2-methyl-1-hexanol 在 lithium diisopropyl amide 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l

文献信息

• Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A
  作者：Carl P. Decicco、Paul Grover

  DOI：10.1021/jo952123l

  日期：1996.1.1

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.