2-(S)-amino-3-boronopropionic acid | 1146616-05-8

• 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: 2-(S)-amino-3-boronopropionic acid
• 英文别名: 2-amino-3-boronopropionic acid；L-Alanine, 3-borono-(9CI)；(2S)-2-amino-3-boronopropanoic acid
• CAS: 1146616-05-8
• 化学式: C₃H₈BNO₄
• 分子量: 132.912
• InChiKey: VZWKSNBNZYZQBJ-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.13
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 盐酸 、 氨 、 silica gel 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以15 mg的产率得到2-(S)-amino-3-boronopropionic acid
  参考文献：
  名称：

  Highly Functionalized Organolithium Reagents for Enantiomerically Pure α-Amino Acid Synthesis

  摘要：

  Highly functionalized L-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic alpha-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.

  DOI：

  10.1021/ol0360039

文献信息

• Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids
  作者：Christopher W. Barfoot、Joanne E. Harvey、Martin N. Kenworthy、John Paul Kilburn、Mahmood Ahmed、Richard J.K. Taylor

  DOI：10.1016/j.tet.2004.10.097

  日期：2005.3

  organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues

  已经产生了衍生自1-丝氨酸的高手性，高度官能化的有机锂试剂，并使其与亲电子试剂反应。然后将由此获得的新型对映体纯的加合物通过β-氨基醇转化为新型的非蛋白生成的α-氨基酸。该方法还提供了一种新型硼酸，然后将其用作Suzuki交叉偶联伴侣，为苯丙氨酸类似物开辟了一条新途径。