methyl (2S)-2-amino-4-(benzyloxy)-3-hydroxybutanoate hydrochloride | 1035919-20-0

• 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: methyl (2S)-2-amino-4-(benzyloxy)-3-hydroxybutanoate hydrochloride
• CAS: 1035919-20-0
• 化学式: C₁₂H₁₇NO₄*ClH
• 分子量: 275.732
• InChiKey: TXTMILRAXGOBSQ-GQNCZFCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.78
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-amino-4-(benzyloxy)-3-hydroxybutanoate hydrochloride 、 二碳酸二叔丁酯 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl 2-(S)-(tert-butoxycarbonyl)amino-3-(S)-hydroxy-4-benzyloxybutanoate 、 methyl 2-(S)-(tert-butoxycarbonyl)amino-3-(R)-hydroxy-4-benzyloxybutanoate
  参考文献：
  名称：

  Enzymatic synthesis of ω-carboxy-β-hydroxy-(l)-α-amino acids

  摘要：

  Commercially available omega-carboxy-aldehydes and glycine have been subjected to the catalytic action of an L-threonine aldolase from Escherichia coli to give the corresponding beta-hydroxy-alpha-(L)-amino acids as a mixture of erythro/threo epimers.Specifically, the reaction with glyoxylic acid (2) gave the epimeric beta-hydroxy-(L)-aspartates (t,e)-9 that could be isolated by ion-exchange chromatography in 67% yield. Following esterification and N-Boc protection, the two epimers could be isolated as pure compounds.Similarly, the aldolase-catalyzed addition of glycine to succinic semialdehyde (4) gave the expected mixture of beta-hydroxy-L-alpha-aminoadipic acids (t)-12 and (e)-12 in 34% yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.070
• 作为产物：
  描述：

  甲醇 、 2-(S)-amino-3-hydroxy-4-benzyloxybutanoic acid 在 氯化亚砜 作用下， 反应 48.0h， 生成 methyl (2S)-2-amino-4-(benzyloxy)-3-hydroxybutanoate hydrochloride
  参考文献：
  名称：

  Enzymatic synthesis of ω-carboxy-β-hydroxy-(l)-α-amino acids

  摘要：

  Commercially available omega-carboxy-aldehydes and glycine have been subjected to the catalytic action of an L-threonine aldolase from Escherichia coli to give the corresponding beta-hydroxy-alpha-(L)-amino acids as a mixture of erythro/threo epimers.Specifically, the reaction with glyoxylic acid (2) gave the epimeric beta-hydroxy-(L)-aspartates (t,e)-9 that could be isolated by ion-exchange chromatography in 67% yield. Following esterification and N-Boc protection, the two epimers could be isolated as pure compounds.Similarly, the aldolase-catalyzed addition of glycine to succinic semialdehyde (4) gave the expected mixture of beta-hydroxy-L-alpha-aminoadipic acids (t)-12 and (e)-12 in 34% yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.070