(2S,3S)-3-hydroxy-2,4,4-trimethylpentanoic acid | 131897-88-6

• 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: (2S,3S)-3-hydroxy-2,4,4-trimethylpentanoic acid
• CAS: 131897-88-6
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: SRACGGODXOHIBL-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2,4,4-trimethylpentanoic acid 、 重氮甲烷 生成 syn-methyl 3-hydroxy-2,4,4-trimethylpentanoate
  参考文献：
  名称：

  HAYASHI, TAMIO;KONISHI, MITSUO;KUMADA, MAKOTO, J. AMER. CHEM. SOC., 1982, 104, N 18, 4963-4965

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3S)-1-((2S,3S)-2,3-Dibutyl-aziridin-1-yl)-3-hydroxy-2,4,4-trimethyl-pentan-1-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 以78%的产率得到(2S,3S)-3-hydroxy-2,4,4-trimethylpentanoic acid
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0

文献信息

• Asymmetric aldol reactions. A new camphor-derived chiral auxiliary giving highly stereoselective aldol reactions of both lithium and titanium(IV) enolates
  作者：Mary Pat Bonner、Edward R. Thornton

  DOI：10.1021/ja00004a034

  日期：1991.2

  camphor-derived N-propionyloxazolidinone effects asymmetric stereochemical control in syn-selective aldol condensations of the derived lithium and titanium (IV) enolates with a variety of aldehydes. Simple and diastereofacial selectivities of the reaction are high, and diastereomeric purities of the crude aldol adducts can be improved, usually by a single recrystallization, to levels of 98-99% in most cases

  一种新的、构象刚性樟脑衍生的 N-丙酰基恶唑烷酮在衍生的锂和钛 (IV) 与各种醛的顺式选择性羟醛缩合反应中实现不对称立体化学控制。该反应的简单和非对映选择性很高，粗醇醛加合物的非对映纯度通常可以通过单次重结晶提高到 98-99% 的水平，在大多数情况下。观察到的面部选择性最好通过过渡结构来解释，其中恶唑烷酮羰基氧和金属之间的分子内螯合诱导烯醇 π 面部分化；观察到的主要产物是螯合控制预期的产物。羟醛加合物的环外羰基水解产生 β-羟基-α-甲基羧酸，随着手性助剂的回收。(R)-2-(苄氧基)丙醛辅音双不对称诱导产生预期的产物来自恶唑烷酮螯合但醛苄氧基非螯合
• Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. 3. Preparation of optically active allylsilanes by palladium-catalyzed asymmetric Grignard cross-coupling
  作者：Tamio Hayashi、Mitsuo Konishi、Yasuo Okamoto、Keiji Kabeta、Makoto Kumada

  DOI：10.1021/jo00370a006

  日期：1986.10
• BONNER, MARY PAT;THORNTON, EDWARD R., J. AMER. CHEM. SOC., 113,(1991) N, C. 1299-1308
  作者：BONNER, MARY PAT、THORNTON, EDWARD R.

  DOI：——

  日期：——
• MONOBACTAMS AND METHODS OF THEIR SYNTHESIS AND USE
  申请人：PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：US20160326157A1

  公开（公告）日：2016-11-10

  Described herein are monobactam antibiotics of Formula (I), (I′), (II), and (II′), along with methods and intermediates for preparing these compounds. Pharmaceutical compositions and methods of treating infectious diseases using the monobactams are also provided.
• US9982005B2
  申请人：——

  公开号：US9982005B2

  公开（公告）日：2018-05-29