(2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid | 156616-29-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid
• 英文别名: (R)-3-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoic acid；(2R)-2-(oxan-2-yloxy)-3-phenylpropanoic acid
• CAS: 156616-29-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: FJCBXKURTHGDPO-PZORYLMUSA-N

物化性质

• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid 在 4-二甲氨基吡啶 、 碳酸二(2-吡啶)酯 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5α-acetyl-13α-[(2'R)-3-phenyllactate]brevifoliol
  参考文献：
  名称：

  Characterization of an abeo-Taxane:  Brevifoliol and Derivatives

  摘要：

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

  DOI：

  10.1021/np0304565
• 作为产物：
  描述：

  D-苯基乳酸甲酯 在 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactic acid
  参考文献：
  名称：

  Characterization of an abeo-Taxane:  Brevifoliol and Derivatives

  摘要：

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

  DOI：

  10.1021/np0304565

文献信息

• Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids
  作者：Sebastian Lüttenberg、Frank Sondermann、Jürgen Scherkenbeck

  DOI：10.1016/j.tet.2011.12.026

  日期：2012.2

  Cyclodepsipeptides of the enniation-, PF1022-, and verticilide-family represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now no stepwise solid-phase synthesis has been accomplished due to the difficult combination of N-methyl amino acids and hydroxycarboxylic acids. We report here the first stepwise solid-phase synthesis

  enniation-、PF1022-和verticilide-家族的环缩缩肽在其多种生物活性方面代表了多种非常有趣的天然产物。然而，由于N-甲基氨基酸和羟基羧酸的组合困难，迄今为止还没有完成逐步固相合成。我们在此报告了基于 Wang-resin 上的 Fmoc/THP-醚保护基策略，首次逐步固相合成驱虫环八肽 PF1022A。我们合成的标准条件可以毫无问题地适应自动肽合成仪。
• Characterization of an <i>a</i><i>beo</i>-Taxane:  Brevifoliol and Derivatives
  作者：Steve Tremblay、Chantal Soucy、Neil Towers、Philip J. Gunning、Livain Breau

  DOI：10.1021/np0304565

  日期：2004.5.1

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.