(3S,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester
• 英文别名: ethyl (3S,4R,5R)-3-acetamido-4,5-dimethyloctanoate
• 化学式: C₁₄H₂₇NO₃
• 分子量: 257.373
• InChiKey: MRPJWWLBJVQZJD-WZRBSPASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2Z,4R,5R)-3-acetylamino-4,5-dimethyl-oct-2-enoic acid ethyl ester 在 catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以The table below provides conversion and ratio of (3R,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester (desired diastereoisomer) to (3S,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester (undesired diastereoisomer) for various hydrogenation catalysts的产率得到(3R,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester
  参考文献：
  名称：

  Amino acids with affinity for the α2δ-protein

  摘要：

  本发明揭示了能够结合到钙通道α2δ亚单位的某些β-氨基酸。这些化合物及其药学上可接受的盐在治疗各种精神疾病、疼痛和其他疾病方面是有用的。本发明还揭示了制备β-氨基酸的方法。

  公开号：

  US07179934B2

文献信息

• Amino acids with affinity for the alpha2delta-protein
  申请人：Blazecka Garth Peter

  公开号：US20050101643A1

  公开（公告）日：2005-05-12

  Certain β-amino acids that bind to the alpha-2-delta (α2δ) subunit of a calcium channel are disclosed. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders. Also disclosed are methods of making the β-amino acids.

  本发明揭示了结合到钙通道的α2δ亚基的某些β-氨基酸。这些化合物及其药学上可接受的盐在治疗各种精神疾病、疼痛和其他疾病方面非常有用。本发明还揭示了制备β-氨基酸的方法。
• AMINO ACIDS WITH AFFINITY FOR THE ALPHA-2-DELTA-PROTEIN
  申请人：Blazecka Garth Peter

  公开号：US20070129550A1

  公开（公告）日：2007-06-07

  Certain β-amino acids that bind to the alpha-2-delta (α2δ) subunit of a calcium channel are disclosed. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders. Also disclosed are methods of making the β-amino acids.

  本文披露了某些能够与钙通道的α2δ亚单位结合的β-氨基酸。这些化合物及其药用盐在治疗多种精神、疼痛和其他疾病方面具有用途。本文还披露了制备β-氨基酸的方法。
• 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
  作者：Ji Zhang、Peter G. Blazecka、Derek A. Pflum、Joseph Bozelak、Derek Vrieze、Norman L. Colbry、Garrett Hoge、David C. Boyles、Brian Samas、Timothy T. Curran、Augustine T. Osuma、Paul Johnson、Suzanne Kesten、Jacob B. Schwarz、Annise Goodman、Mark Plummer、Anne Akin、Yun Huang、Michael Lovdahl、Andrew J. Thorpe

  DOI：10.1016/j.tetlet.2008.12.111

  日期：2009.3

  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.
• US7179934B2
  申请人：——

  公开号：US7179934B2

  公开（公告）日：2007-02-20
• US7388023B2
  申请人：——

  公开号：US7388023B2

  公开（公告）日：2008-06-17