(3S,4R,5R)-tribenzyloxy-(6S)-hydroxyocta-1,7-diene | 195873-73-5

• 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: (3S,4R,5R)-tribenzyloxy-(6S)-hydroxyocta-1,7-diene
• 英文别名: (3S,4R,5R,6S)-4,5,6-tris(phenylmethoxy)octa-1,7-dien-3-ol
• CAS: 195873-73-5
• 化学式: C₂₉H₃₂O₄
• 分子量: 444.571
• InChiKey: QJGUSTGOXFWUJQ-QUAHOIDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-tribenzyloxy-(6S)-hydroxyocta-1,7-diene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene
  参考文献：
  名称：

  Synthesis of cyclitols via ring-closing metathesis

  摘要：

  A convenient synthesis of enantiomerically pure and differentially protected L-chiro- and myo-inositols as well as conduritols B and F from 2,3,4-tri-O-benzyl-D-xylopyranose via ring-closing metathesis is reported. The facile synthesis of conduritol B constitutes a short formal synthesis of (-)-cyclophellitol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00065-8
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-xylopyranose 在 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3S,4R,5R)-tribenzyloxy-(6S)-hydroxyocta-1,7-diene
  参考文献：
  名称：

  Synthesis of cyclitols via ring-closing metathesis

  摘要：

  A convenient synthesis of enantiomerically pure and differentially protected L-chiro- and myo-inositols as well as conduritols B and F from 2,3,4-tri-O-benzyl-D-xylopyranose via ring-closing metathesis is reported. The facile synthesis of conduritol B constitutes a short formal synthesis of (-)-cyclophellitol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00065-8

文献信息

• Synthesis of Differentially Protected<i>myo</i>- and<i>chiro</i>-Inositols from<scp>d</scp>-Xylose: Stereoselectivity in Intramolecular SmI₂-Promoted Pinacol Reactions
  作者：Alexander Kornienko、Marc d’Alarcao、Giovanni Luchetti、Kejia Ding

  DOI：10.1055/s-2008-1067259

  日期：2008.10

  Methods for the enantioselective conversion of d-xylose into differentially protected myo-inositol and l-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI2-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explanations for this behavior are discussed.

  已开发出将d-木糖选择性转化为不同保护形式的肌醇和l-奇霉醇的方法。关键转化是高度的非对映选择性内分子SmI2促成的皮那克尔耦合。立体选择性极度依赖于反应条件，提示机制可能发生变化。讨论了初步的机制实验及对此行为的可能解释。
• Enantio- and Diastereodivergent Synthetic Route to Multifarious Cyclitols from<scp>d</scp>-Xylose via Ring-Closing Metathesis
  作者：Marc d’Alarcao、Alexander Kornienko、Giovanni Luchetti、Kejia Ding

  DOI：10.1055/s-2008-1067260

  日期：2008.10

  Short stereoselective syntheses of various cyclitols, including the derivatives of conduritol B, conduritol F, myo-inositol, and chiro-inositol have been accomplished. The key steps in the syntheses are a ring-closing metathesis process and a diastereodivergent organometallic addition to a d-xylose-derived aldehyde.

  已经完成了多种环醇的立体选择性合成，包括康杜醇B、康杜醇F、肌醇及手性肌醇的衍生物。合成的关键步骤是一种环闭合的金属催化的交叉偶联反应和一种针对由d-木糖衍生的醛所进行的手性金属有机加成反应。简言之，我们通过特定的立体化学操作，巧妙地设计并实施了一系列有机合成策略，成功地构建了这些结构复杂且功能独特的天然环醇类化合物，为相关领域的深入研究奠定了坚实的物质基础。