(2R*,3R*)-ethyl 3-acetoxy-2-bromo-3-cyclohexylpropionate | 132377-75-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R*,3R*)-ethyl 3-acetoxy-2-bromo-3-cyclohexylpropionate
• 英文别名: ethyl (2S,3S)-3-acetyloxy-2-bromo-3-cyclohexylpropanoate
• CAS: 132377-75-4
• 化学式: C₁₃H₂₁BrO₄
• 分子量: 321.211
• InChiKey: IXRXCUBGBXXBSX-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S*,3R*)-ethyl 3-cyclohexy-2,3-dihydroxypropionate 、 溶剂黄146 在 氢溴酸 作用下， 反应 1.0h， 以88%的产率得到(2R*,3R*)-ethyl 3-acetoxy-2-bromo-3-cyclohexylpropionate
  参考文献：
  名称：

  Selective transformations of threo-2,3-dihydroxy esters

  摘要：

  Two highly regio- and stereoselective transformation of threo-2,3-dihydroxy esters have been developed. In the first reaction, the alpha-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the alpha-tosylates and alpha-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield. The alpha-nosylates are also suitable electrophiles for azides, giving access to erythro-alpha-azido-beta-hydroxy esters. The second reaction involves conversion of the diol esters to acetoxy bromo esters. The beta-substituent plays a key role in determining the regiochemistry since cases with beta-alkyl substituents afford beta-acetoxy-alpha-bromo esters exclusively, whereas a beta-phenyl substituent directs formation of the alpha-acetoxy-beta-bromo ester. The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.

  DOI：

  10.1021/jo00008a051