(4R,5R)-3-methoxyimino-4,5-dimethyl-octanoic acid ethyl ester | 1135141-66-0

• 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: (4R,5R)-3-methoxyimino-4,5-dimethyl-octanoic acid ethyl ester
• CAS: 1135141-66-0
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: MCHTWZUHCFFBTR-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-3-methoxyimino-4,5-dimethyl-octanoic acid ethyl ester 在 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到(2Z,4R,5R)-3-amino-4,5-dimethyl-oct-2-enoic acid ethyl ester
  参考文献：
  名称：

  The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein

  摘要：

  A chiral beta-amino acid containing three contiguous chiral centers was synthesized efficiently in 11 steps, employing enantio-enriched beta-ketoester as a key intermediate, via stereoselective catalytic hydrogenation of the corresponding enamide. Stereoselective 1,4-addition of a methyl group and protonation were key to the preparation of the desired acid 12. Mild and efficient reaction conditions were applied to the enamine formation and protection to avoid epimerization at C-4 of compounds 13 and 14. The final compound was found to display potent affinity for the alpha(2)delta-protein that is a recognized drug target for the treatment of a variety of diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.111
• 作为产物：
  描述：

  (4R,5R)-4,5-dimethyl-3-oxo-octanoic acid ethyl ester 、 甲氧基胺盐酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以97%的产率得到(4R,5R)-3-methoxyimino-4,5-dimethyl-octanoic acid ethyl ester
  参考文献：
  名称：

  The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein

  摘要：

  A chiral beta-amino acid containing three contiguous chiral centers was synthesized efficiently in 11 steps, employing enantio-enriched beta-ketoester as a key intermediate, via stereoselective catalytic hydrogenation of the corresponding enamide. Stereoselective 1,4-addition of a methyl group and protonation were key to the preparation of the desired acid 12. Mild and efficient reaction conditions were applied to the enamine formation and protection to avoid epimerization at C-4 of compounds 13 and 14. The final compound was found to display potent affinity for the alpha(2)delta-protein that is a recognized drug target for the treatment of a variety of diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.111