(2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate | 132377-77-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate
• CAS: 132377-77-6
• 化学式: C₉H₁₇BrO₃
• 分子量: 253.136
• InChiKey: MBSOVWMKTCZGSR-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以88%的产率得到3-羟基辛酸甲酯
  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
• 作为产物：
  描述：

  (2S,3R)-(+)-methyl 2,3-dihydroxyoctanoate 、 溶剂黄146 在 甲醇 、 氢溴酸 作用下， 生成 (2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate
  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