methyl (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactate | 195877-62-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactate
• CAS: 195877-62-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: XITMEFBJDZMRQN-KWCCSABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactate 在 4-二甲氨基吡啶 、 碳酸二(2-吡啶)酯 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 5α-acetyl-13α-[(2'R)-O-(tetrahydropyran-2-yl)-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-3-苯乳酸 在 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 methyl (2R)-(+)-O-(tetrahydropyran-2-yl)-3-phenyllactate
  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