(-)-erythro-γ-Hydroxynorvaline | 3209-39-0

• 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: (-)-erythro-γ-Hydroxynorvaline
• 英文别名: (R,R)-syn-γ-hydroxynorvaline；(2R,4R)-2-amino-4-hydroxypentanoic acid
• CAS: 3209-39-0；21704-88-1；21704-96-1；69223-00-3；94799-22-1；117248-95-0；117248-96-1
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: SBRVJFMQKPUAGQ-QWWZWVQMSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  343.3±32.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+)-(3R,5R)-3-Amino-5-methyldihydro-2(3H)-furanone hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (-)-erythro-γ-Hydroxynorvaline
  参考文献：
  名称：

  Enantioselective Synthesis of γ-Hydroxynorvaline

  摘要：

  本文介绍了一种对映体纯δ-羟基缬氨酸的新合成方法。关键步骤是用易于从环氧丙烷制备的伯碘衍生物 2 对手性希夫碱 1 进行非对映选择性烷基化。

  DOI：

  10.1055/s-1997-3246

文献信息

• Stereoselective Synthesis of syn-γ-Hydroxynorvaline and Related α-Amino Acids
  作者：Dominika Valachová、Branislav Ferko、Eva Puchľová、Oľga Caletková、Dušan Berkeš、Andrej Kolarovič、Pavol Jakubec

  DOI：10.1055/s-0039-1690705

  日期：2019.12

  non-proteinogenic amino acids, l-norvaline, γ-oxonorvaline, and syn-γ-hydroxynorvaline, are reported. The chromatography-free route pivoted on the construction of highly enantiomerically enriched substituted α-amino-γ-oxopentanoic acid, from which all three members were accessed divergently via chemoselective and stereoselective reductions. The rapid synthesis of this key α-amino-γ-oxopentanoic acid was achieved

  The total syntheses of three enantiomerically pure non-proteinogenic amino acids, l-norvaline, γ-oxonorvaline, and syn-γ-hydroxynorvaline, are reported. The chromatography-free route pivoted on the construction of highly enantiomerically enriched substituted α-amino-γ-oxopentanoic acid, from which all three members were accessed divergently via chemoselective and stereoselective reductions. The rapid
• Enantioselective synthesis of hydroxy α-amino acids. (-)-- and (-) --γ-hydroxynorvalines
  作者：Jesus Ariza、Josep Font、Rosa M. Ortuño

  DOI：10.1016/s0040-4020(01)89761-1

  日期：1990.1
• ARIZA, JESUS;FONT, JOSEP;ORTUNO, ROSA M., TETRAHEDRON, 46,(1990) N, C. 1931-1942
  作者：ARIZA, JESUS、FONT, JOSEP、ORTUNO, ROSA M.

  DOI：——

  日期：——
• HARDING, KENN E.;MARMAN, THOMAS H.;NAM, DO-HYUN, TETRAHEDRON LETT., 29,(1988) N 14, 1627-1630
  作者：HARDING, KENN E.、MARMAN, THOMAS H.、NAM, DO-HYUN

  DOI：——

  日期：——
• Enantioselective Synthesis of γ-Hydroxynorvaline
  作者：M. Jacob、M. Roumestant、P. Viallefont、J. Martinez

  DOI：10.1055/s-1997-3246

  日期：1997.6

  A new synthesis of enantiomerically pure γ-hydroxynorvaline is described. The key step involves diastereoselective alkylation of the chiral Schiff base 1 with primary iodo derivatives 2 easily prepared from propylene oxide.

  本文介绍了一种对映体纯δ-羟基缬氨酸的新合成方法。关键步骤是用易于从环氧丙烷制备的伯碘衍生物 2 对手性希夫碱 1 进行非对映选择性烷基化。