(3S)-3-[(tert-butoxy)carbonyl]-4,4-dimethylpentanoic acid | 1408184-21-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-[(tert-butoxy)carbonyl]-4,4-dimethylpentanoic acid
• 英文别名: (3S)-4,4-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]pentanoic acid
• CAS: 1408184-21-3
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: SGSBQMXLSBZUDD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(tert-butoxy)carbonyl]-4,4-dimethylpentanoic acid 在 叠氮磷酸二苯酯 、 palladium on activated carbon 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 9.5h， 生成 (2R)-2-(aminomethyl)-3,3-dimethylbutanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis ofβ²-homo-tert-LeucineviaRadical Addition to EnantiopureN-Fumaroylhexahydrobenzooxazolidin-2-one

  摘要：

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.

  DOI：

  10.1002/hlca.201200448
• 作为产物：
  描述：

  富马酸叔-丁酯 在 正丁基锂 、 lithium hydroxide monohydrate 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 (3S)-3-[(tert-butoxy)carbonyl]-4,4-dimethylpentanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis ofβ²-homo-tert-LeucineviaRadical Addition to EnantiopureN-Fumaroylhexahydrobenzooxazolidin-2-one

  摘要：

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.

  DOI：

  10.1002/hlca.201200448

文献信息

• Asymmetric Synthesis of<i>β</i>²-homo-<i>tert</i>-Leucine<i>via</i>Radical Addition to Enantiopure<i>N</i>-Fumaroylhexahydrobenzooxazolidin-2-one
  作者：Margarita Escudero-Casao、Eusebio Juaristi

  DOI：10.1002/hlca.201200448

  日期：2012.10

  Abstractβ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.