(E)-(4R,6R,8S)-6-benzyloxy-4,9-bis(2,2-dimethylpropionyloxy)-8-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester | 300579-02-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-(4R,6R,8S)-6-benzyloxy-4,9-bis(2,2-dimethylpropionyloxy)-8-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (E,4R,6S,8S)-4,9-bis(2,2-dimethylpropanoyloxy)-8-hydroxy-6-phenylmethoxynon-2-enoate
• CAS: 300579-02-6
• 化学式: C₄₂H₆₀O₈
• 分子量: 692.934
• InChiKey: DCUQICKFRGXWMB-NTLWGKBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(4R,6R,8S)-6-benzyloxy-4,9-bis(2,2-dimethylpropionyloxy)-8-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 在 四氧化锇 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium tetrahydroborate 、 新铜试剂 、 N-甲基吗啉氧化物 、 高碘酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 0.83h， 生成 2,2-Dimethyl-propionic acid (2S,4R,6R)-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  A Versatile Stereocontrolled Approach to Chiral Tetrahydrofuran and Tetrahydropyran Derivatives via Sequential Asymmetric Horner−Wadsworth−Emmons and Palladium-Catalyzed Ring Closure Reactions

  摘要：

  [GRAPHICS]An approach to chiral tetrahydrofuran and tetrahydropyran derivatives Is reported which is based on the sequential use of an asymmetric Horner-Wadsworth-Emmons desymmetrization of a meso dialdehyde and a palladium-catalyzed intramolecular allylic substitution. The strategy is versatile in that either a cis- or a trans-relation between the stereocenters adjacent to the ring oxygen can be obtained.

  DOI：

  10.1021/ol006135r
• 作为产物：
  描述：

  (E)-(4R,6R,8S)-6-Benzyloxy-4,8-bis-(2,2-dimethyl-propionyloxy)-9-hydroxy-non-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 在 咪唑 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以59%的产率得到(E)-(4R,6R,8S)-6-benzyloxy-4,9-bis(2,2-dimethylpropionyloxy)-8-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
  参考文献：
  名称：

  A Versatile Stereocontrolled Approach to Chiral Tetrahydrofuran and Tetrahydropyran Derivatives via Sequential Asymmetric Horner−Wadsworth−Emmons and Palladium-Catalyzed Ring Closure Reactions

  摘要：

  [GRAPHICS]An approach to chiral tetrahydrofuran and tetrahydropyran derivatives Is reported which is based on the sequential use of an asymmetric Horner-Wadsworth-Emmons desymmetrization of a meso dialdehyde and a palladium-catalyzed intramolecular allylic substitution. The strategy is versatile in that either a cis- or a trans-relation between the stereocenters adjacent to the ring oxygen can be obtained.

  DOI：

  10.1021/ol006135r

文献信息

• A Versatile Stereocontrolled Approach to Chiral Tetrahydrofuran and Tetrahydropyran Derivatives by Use of Sequential Asymmetric Horner−Wadsworth−Emmons and Ring-Closure Reactions
  作者：Lauri Vares、Tobias Rein

  DOI：10.1021/jo0259111

  日期：2002.10.1

  use of an asymmetric Horner-Wadsworth-Emmons reaction and a cyclization step is presented. The approach is both stereochemically and structurally versatile since three different cyclization methods can be employed starting from the same HWE product: (i) palladium-catalyzed substitution, (ii) hetero-Michael addition, or (iii) epoxide opening. The asymmetric HWE reaction controls the absolute configuration

  提出了一种基于顺序使用不对称的霍纳-沃兹沃思-埃蒙斯反应和环化步骤的手性四氢呋喃和四氢吡喃衍生物的方法。该方法在立体化学和结构上都是通用的，因为可以从相同的HWE产品开始使用三种不同的环化方法：（i）钯催化的取代，（ii）杂-迈克尔加成，或（iii）环氧开放。不对称的HWE反应控制最终产物的绝对构型，而相对构型则受HWE反应中几何选择性和相应环化方法的立体化学的综合影响控制。