(4S,5S)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid | 81322-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid
• CAS: 81322-84-1
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: WQOUSSHMBFCZNC-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S,5S)-N-benzyloxycarbonyl-5-hydroxy-4-isobutyl-1,3-oxazinan-6-one 在 lithium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.17h， 生成 (4S,5S)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones

  摘要：

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.

  DOI：

  10.1021/jo0700326

文献信息

• Renin inhibitors. Substitution of the leucyl residues of Leu-Leu-Val-Phe-OCH3 with 3-amino-2-hydroxy-5-methylhexanoic acid
  作者：Rodney L. Johnson

  DOI：10.1021/jm00347a024

  日期：1982.5

  The 2S,3S and 2R,3S diastereoisomers of the hydroxy amino acid 3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA) were synthesized and substituted for the leucyl residues of Leu-Leu-Val-Phe-OCH3 to yield the following analogues: AHMHA-Leu-Val-Phe-OCH3, AHMHA-Val-Phe-OCH3, and Leu-AHMHA-Val-Phe-OCH3. These analogues were tested in vitro for their ability to inhibit human amniotic renin. All of the analogues were found to inhibit renin to some extent with inhibitory constants in the range of 10(-3) to 10(-4) M. The analogues AHMHA-Leu-Val-Phe-OCH3 and AHMHA-Val-Phe-OCH3 exhibited competitive inhibition when the 2S,3S isomer of AHMHA was employed and noncompetitive kinetics when the 2R,3S isomer of AHMHA was used. For the Leu-AHMHA-Val-Phe-OCH3 analogues, competitive kinetics were observed regardless of the isomer of AHMHA employed. These latter analogues also proved to be the most active in the above series.