ethyl (2Z,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

• 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: ethyl (2Z,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate
• 英文别名: ethyl (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-phenylbut-2-enoate
• 化学式: C₁₈H₂₈O₃Si
• 分子量: 320.504
• InChiKey: MKXDVROCILHXJS-FIPLFPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-扁桃酸 在 diisobutylammonium hydride 、 sequential acid 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 ethyl (2Z,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate
  参考文献：
  名称：

  简明全合成（+）-goniofufurone和goniobutenolides A和B

  摘要：

  通过（R）-（-）-扁桃酸经β-羟基砜4作为常见中间体，以光学和非对映体纯的形式制备了细胞毒性的苯乙烯基内酯，（+）-gonfufufurone和goniobutenolides A和B。

  DOI：

  10.1016/0040-4039(96)00820-9

文献信息

• Concise Stereoselective Total Synthesis of Leiocarpin C
  作者：Dasireddi Chandra Rao、Vanam Shekhar、Dorigondla Kumar Reddy、Baggu Chinnababu、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.201200656

  日期：2013.12

  A simple and highly concise strategy has been developed for the stereoselective total synthesis of leiocarpin C starting from commercially available mandelic ester. The strategy utilizes the OsO4‐catalyzed cis‐hydroxylation and selective reduction with K‐Selectride as key steps.

  已经开发了一种简单且高度简洁的策略，用于从商业可得的扁桃酸酯开始立体选择性地合成徕卡霉素C。该策略利用了OsO 4催化的顺式羟基化和K-Selectride选择性还原的关键步骤。
• First total synthesis of (+)-crassalactone A
  作者：V. Shekhar、D. Kumar Reddy、V. Suresh、D. Chanti Babu、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2009.12.038

  日期：2010.2

  A simple and highly efficient first total synthesis Of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropiolate to a chiral aldehyde intermediate as key steps. (C) 2009 Elsevier Ltd. All rights reserved.
• Easy access to an enantiopure precursor of (+)-goniodiol
  作者：Jean-Philippe Surivet、Jean-Noël Volle、Jean-Michel Vatèle

  DOI：10.1016/0957-4166(96)00431-4

  日期：1996.11

  Asymmetric synthesis of the epoxide 2 has been achieved from (R)-mandelic acid 3 via highly diastereoselective Wittig reaction and erythro-selective OsO4 catalyzed cis-hydroxylation as key steps. Copyright (C) 1996 Elsevier Science Ltd
• Concise total synthesis of (+)-goniofufurone and goniobutenolides A and B
  作者：Jean-Philippe Surivet、Jean-Michel Vatèle

  DOI：10.1016/0040-4039(96)00820-9

  日期：1996.6

  Cytotoxic styryl lactones, (+)-goniofufurone and goniobutenolides A and B have been prepared in optically and diastereomerically pure form from (R)-(−)-mandelic acid via the β-hydroxy sulfone 4 as a common intermediate.

  通过（R）-（-）-扁桃酸经β-羟基砜4作为常见中间体，以光学和非对映体纯的形式制备了细胞毒性的苯乙烯基内酯，（+）-gonfufufurone和goniobutenolides A和B。