(S)-2-Amino-6-(dihydroxyboryl)hexanoic acid hydrochloride | 194656-75-2

• 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: (S)-2-Amino-6-(dihydroxyboryl)hexanoic acid hydrochloride
• 英文别名: 2(S)-amino-6-boronohexanoic acid hydrochloride；2(S)-amino-6-boronohexanoic Acid, Hydrochloride Salt；Abh hydrochloride；(2S)-2-amino-6-boronohexanoic acid;hydrochloride
• CAS: 194656-75-2
• 化学式: C₆H₁₄BNO₄*ClH
• 分子量: 211.453
• InChiKey: XCUVEZUCSHVMRK-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  104
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2(S)-amino-6-boronohexanoic acid ammonium salt 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到(S)-2-Amino-6-(dihydroxyboryl)hexanoic acid hydrochloride
  参考文献：
  名称：

  Improved and High Yield Synthesis of the Potent Arginase Inhibitor:  2(S)-Amino-6-boronohexanoic Acid

  摘要：

  A simple three-step synthesis of the potent arginase inhibitor 2(S)-amino-6-boronohexanoic acid (ABH) has been developed. The key step was alkylation of the Ni-II complex of the Schiff base derived from glycine and (S)-2-[N'-(N-benzylprolyl)amino]benzophenone (BPB) with pinacol 4-bromobutylboronate. Acidic hydrolysis afforded ABH in 50% overall yield, high enantiomeric excess, and quantitative recovery of the chiral auxiliary.

  DOI：

  10.1021/op050096n

文献信息

• Concise synthesis of ω-borono-α-amino acids
  作者：Venkata Jaganmohan Reddy、J. Subash Chandra、M. Venkat Ram Reddy

  DOI：10.1039/b618750a

  日期：——

  A short protocol for the practical scale synthesis of several ω-borono-α-amino acids is described via the alkylation of benzophenone glycinimines with various electrophiles.

  本文描述了一种简短的协议，用于通过将苯基酮甘氨酸亚胺与多种电亲体烷基化，实用规模合成几种ω-硼烷-α-氨基酸。
• Improved and High Yield Synthesis of the Potent Arginase Inhibitor:  2(<i>S</i>)-Amino-6-boronohexanoic Acid
  作者：Sandrine Vadon-Legoff、Sylvie Dijols、Daniel Mansuy、Jean-Luc Boucher

  DOI：10.1021/op050096n

  日期：2005.9.1

  A simple three-step synthesis of the potent arginase inhibitor 2(S)-amino-6-boronohexanoic acid (ABH) has been developed. The key step was alkylation of the Ni-II complex of the Schiff base derived from glycine and (S)-2-[N'-(N-benzylprolyl)amino]benzophenone (BPB) with pinacol 4-bromobutylboronate. Acidic hydrolysis afforded ABH in 50% overall yield, high enantiomeric excess, and quantitative recovery of the chiral auxiliary.