methyl (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactate | 215596-66-0

• 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 (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactate
• 英文别名: 3-Phenyl-(2S)-2-(tetrahydro-pyran-2-yloxy)-propionic Acid Methyl Ester；methyl (2S)-2-(oxan-2-yloxy)-3-phenylpropanoate
• CAS: 215596-66-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: XITMEFBJDZMRQN-LSLKUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-(-)-O-(tetrahydropyran-2-yl)-3-phenyllactate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以82%的产率得到(2S)-(-)-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
• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 在 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 methyl (2S)-(-)-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

文献信息

• Piperizinones as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030144277A1

  公开（公告）日：2003-07-31

  The present application describes modulators of CCR3 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了公式（I）的CCR3调节剂或其药用盐形式，用于预防哮喘和其他过敏性疾病。
• MASH, EUGENE A.;ARTERBURN, JEFFREY B.;FRYLING, JAMES A.;MITCHELL, SUSAN H+, J. ORG. CHEM., 56,(1991) N, C. 1088-1093
  作者：MASH, EUGENE A.、ARTERBURN, JEFFREY B.、FRYLING, JAMES A.、MITCHELL, SUSAN H+

  DOI：——

  日期：——
• US6974869B2
  申请人：——

  公开号：US6974869B2

  公开（公告）日：2005-12-13
• US7514430B2
  申请人：——

  公开号：US7514430B2

  公开（公告）日：2009-04-07
• [EN] PIPERIZINONES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] PIPERAZINONES DE MODULATION DE L'ACTIVITE DES RECEPTEURS DES CHIMIOKINES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003024401A2

  公开（公告）日：2003-03-27

  The present application describes modulators of CCR3 of formula (I) or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.