(4R)-3-[(2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one | 460352-60-7

• 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: (4R)-3-[(2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2S,3R)-2-methyl-5-phenyl-3-prop-2-enoxypentanoyl]-1,3-oxazolidin-2-one
• CAS: 460352-60-7
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: GYRNMKBZZUMZTF-AJSBUHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 生成 (2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoic acid
  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：

  (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 三氟甲磺酸 、 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 5.0h， 生成 (4R)-3-[(2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoyl]-4-benzyl-1,3-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

• 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.