(S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methyldodecanoyl)oxazolidin-2-one | 460352-58-3

• 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: (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methyldodecanoyl)oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methyldodecanoyl]-1,3-oxazolidin-2-one
• CAS: 460352-58-3
• 化学式: C₂₃H₃₅NO₄
• 分子量: 389.535
• InChiKey: FHNRBVVVOKWCRN-SESVDKBCSA-N

物化性质

• 沸点：
  545.0±33.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methyldodecanoyl)oxazolidin-2-one 在 盐酸 、 lithium hydroxide 、 三氟甲磺酸 、 叠氮磷酸二苯酯 、 双氧水 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 生成 (1S,2R)-2-Allyloxy-1-methyl-undecylamine
  参考文献：
  名称：

  Synthesis of Cyclic Peptidomimetics from Aldol Building Blocks

  摘要：

  Aldol products (3-hydroxy acids) with an allylprotected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.

  DOI：

  10.1021/jo025889b
• 作为产物：
  描述：

  癸醛 、 (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methyldodecanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of Cyclic Peptidomimetics from Aldol Building Blocks

  摘要：

  Aldol products (3-hydroxy acids) with an allylprotected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.

  DOI：

  10.1021/jo025889b

文献信息

• A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes
  作者：Matt Cheeseman、Iwan R. Davies、Phil Axe、Andrew L. Johnson、Steven D. Bull

  DOI：10.1039/b908600e

  日期：——

  A novel way of combining chiral auxiliaries and substrate directable reactions is described that employs a three-step sequence of aldol/cyclopropanation/retro-aldol reactions for the asymmetric synthesis of enantiopure cyclopropane-carboxaldehydes. In the first step, reaction of the boron enolate of (S)-N-propionyl-5,5-dimethyl-oxazolidin-2-one with a series of α,β-unsaturated aldehydes affords their

  描述了一种将手性助剂和底物可直接反应相结合的新方法，该方法采用三步顺序的醛醇/环丙烷化/复古-醛醇反应用于对映纯环丙烷-甲醛的不对称合成。第一步，硼氢化硼的反应（S）-N-丙酰基-5,5-二甲基-恶唑烷-2-具有一系列α，β-不饱和醛的化合物可以提供高纯度的相应的顺式-羟醛产物。在第二步中，在它们的“临时”β-羟基立体中心的立体定向作用下，对这些顺式-羟醛的烯烃官能团进行定向环丙烷化，从而得到一系列高环式的环丙基-羟醛。最后，这些环丙基-醇醛的锂醇盐的逆-醇醛解离导致它们的临时β-羟基立体中心的破坏，从而以> 95％ee提供母体手性助剂和手性环丙烷-甲醛。已经证明该方法的潜力以高收率不对称地合成了含环丙烷的天然产物卡斯卡利酸。
• Synthesis of Cyclic Peptidomimetics from Aldol Building Blocks
  作者：Sanjita Sasmal、Armin Geyer、Martin E. Maier

  DOI：10.1021/jo025889b

  日期：2002.8.1

  Aldol products (3-hydroxy acids) with an allylprotected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.