(R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid pentafluorophenyl ester | 289622-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2R)-2-[(4S,5S)-2,2,4-trimethyl-3-[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoyl]-1,3-oxazolidin-5-yl]propanoate
• CAS: 289622-61-3
• 化学式: C₂₄H₃₁F₅N₂O₆
• 分子量: 538.512
• InChiKey: OVSQIWOWMUYZAJ-LEGQTRPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid pentafluorophenyl ester 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (S)-N-[(1S,2S,3R)-2-Hydroxy-4-((R)-5-isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1,3-dimethyl-4-oxo-butyl]-2-methylamino-propionamide
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5
• 作为产物：
  描述：

  五氟苯酚 、 (R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以89%的产率得到(R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5

文献信息

• Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin
  作者：Assunta Giordano、Carmela Della Monica、Francesco Landi、Aldo Spinella、Guido Sodano

  DOI：10.1016/s0040-4039(00)00533-5

  日期：2000.5

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.