(4S)-3-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 88635-99-8

• 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)-3-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 88635-99-8
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: BXAJPFDEGSQVNX-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.5h， 生成 tert-Butyl syn-(4S,5R)-5-hydroxy-4-methyl-3-oxohexanoate
  参考文献：
  名称：

  Simple and Efficient Synthesis of (+)-Methyl 7-Benzoylpederate, a Key Intermediate toward the Mycalamides

  摘要：

  [GRAPHICS]A simple and efficient method for the synthesis of (+)-methyl 7-benzoylpederate, the left half of pederin, mycalamides, onnamides, and theopederins, was developed, The key reactions include the Evans asymmetric aldol reaction, a thioacetalization-lactonization, a stereoselective Claisen condensation, and a Takai-Nozaki olefination, The synthesis requires only nine steps and proceeds in 26% overall yield.

  DOI：

  10.1021/ol990936g
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 、 乙醛 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 以91%的产率得到(4S)-3-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Simple and Efficient Synthesis of (+)-Methyl 7-Benzoylpederate, a Key Intermediate toward the Mycalamides

  摘要：

  [GRAPHICS]A simple and efficient method for the synthesis of (+)-methyl 7-benzoylpederate, the left half of pederin, mycalamides, onnamides, and theopederins, was developed, The key reactions include the Evans asymmetric aldol reaction, a thioacetalization-lactonization, a stereoselective Claisen condensation, and a Takai-Nozaki olefination, The synthesis requires only nine steps and proceeds in 26% overall yield.

  DOI：

  10.1021/ol990936g

文献信息

• Asymmetric acylation reactions of chiral imide enolates. The first direct approach to the construction of chiral .beta.-dicarbonyl synthons
  作者：D. A. Evans、M. D. Ennis、T. Le、N. Mandel、G. Mandel

  DOI：10.1021/ja00316a077

  日期：1984.2

  Acylation de 2 propionimides chirales: isopropyl-4 propionyl-3 oxazolidone-2 et methyl-4 phenyl-5 propionyl-3 oxazolidone-2

  酰化 2 propionimides 手性：isopropyl-4 propionyl-3 oxazolidone-2 etmethyl-4 phenyl-5 propionyl-3 oxazolidone-2
• Enantioselective aldol condensations: The use of ketone boron enolates with chiral ligands attached to boron.
  作者：Ian Paterson、M.Anne Lister、Cynthia K McClure

  DOI：10.1016/s0040-4039(00)85065-0

  日期：1986.1

  Aldol condensation between diethylketone and simple aldehydes using(lpc)2BOTf/iPr2NEt in CH2Cl2 gives syn-adducts in good ee (66–90%) and with high diastereoselectivity(≥90%). Other chiral dialkylboron triflate reagents examined give lower ees.

  使用（LPC）和二乙基醛简单之间的醛醇缩合2 BOTf /我镨2净在CH 2氯2给出顺式良好EE（66-90％）中，用高非对映选择性（≥90％）-adducts。检查的其他手性二烷基硼酸三氟甲磺酸盐试剂可提供较低的ee。
• Enantioselective Total Synthesis and Structure Determination of the Antiherpetic Anthrapyran Antibiotic AH-1763 IIa
  作者：Lutz F. Tietze、Kersten M. Gericke、Ramakrishna Reddy Singidi

  DOI：10.1002/anie.200601992

  日期：2006.10.27
• Simple and Efficient Synthesis of (+)-Methyl 7-Benzoylpederate, a Key Intermediate toward the Mycalamides
  作者：Nicholas S. Trotter、Shunya Takahashi、Tadashi Nakata

  DOI：10.1021/ol990936g

  日期：1999.9.1

  [GRAPHICS]A simple and efficient method for the synthesis of (+)-methyl 7-benzoylpederate, the left half of pederin, mycalamides, onnamides, and theopederins, was developed, The key reactions include the Evans asymmetric aldol reaction, a thioacetalization-lactonization, a stereoselective Claisen condensation, and a Takai-Nozaki olefination, The synthesis requires only nine steps and proceeds in 26% overall yield.