(5S)-5-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pyrrolidine-2,4-dione | 1401229-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S)-5-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pyrrolidine-2,4-dione
• CAS: 1401229-64-8
• 化学式: C₁₇H₂₅NO₃Si
• 分子量: 319.476
• InChiKey: NGXMVIREGOODGL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pyrrolidine-2,4-dione 、 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到[(2S)-2-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]-5-oxo-1,2-dihydropyrrol-3-yl] (E,2S,4R)-2,4,6-trimethylnon-6-enoate
  参考文献：
  名称：

  First Total Synthesis of Epicoccarine A via O- to C-Acyl Rearrangement Strategy

  摘要：

  The first total synthesis of antibacterial epicoccarine A isolated from a fungus Epicoccum sp. has been accomplished in 10 steps along with synthetic elaboration of its C5-epimer, highlighting the utility of O- to C-acyl rearrangement of a 4-O-acyltetramic acid derivative. Comparison of spectroscopic properties and specific optical rotations of the synthetic samples with those reported for authentic material has clearly indicated the unspecified absolute stereochemistry of this natural product to be 5S.

  DOI：

  10.1021/ol3024506
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 咪唑 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (5S)-5-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pyrrolidine-2,4-dione
  参考文献：
  名称：

  First Total Synthesis of Epicoccarine A via O- to C-Acyl Rearrangement Strategy

  摘要：

  The first total synthesis of antibacterial epicoccarine A isolated from a fungus Epicoccum sp. has been accomplished in 10 steps along with synthetic elaboration of its C5-epimer, highlighting the utility of O- to C-acyl rearrangement of a 4-O-acyltetramic acid derivative. Comparison of spectroscopic properties and specific optical rotations of the synthetic samples with those reported for authentic material has clearly indicated the unspecified absolute stereochemistry of this natural product to be 5S.

  DOI：

  10.1021/ol3024506

文献信息

• First Total Synthesis of Epicoccarine A via <i>O</i>- to <i>C</i>-Acyl Rearrangement Strategy
  作者：Yasuaki Ujihara、Ken Nakayama、Tetsuya Sengoku、Masaki Takahashi、Hidemi Yoda

  DOI：10.1021/ol3024506

  日期：2012.10.5

  The first total synthesis of antibacterial epicoccarine A isolated from a fungus Epicoccum sp. has been accomplished in 10 steps along with synthetic elaboration of its C5-epimer, highlighting the utility of O- to C-acyl rearrangement of a 4-O-acyltetramic acid derivative. Comparison of spectroscopic properties and specific optical rotations of the synthetic samples with those reported for authentic material has clearly indicated the unspecified absolute stereochemistry of this natural product to be 5S.