(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid | 1369492-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid
• 英文别名: (4r,7r,e)-7-(t-Butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoic acid；(E,4R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[(4-methoxyphenyl)methoxy]oct-2-enoic acid
• CAS: 1369492-89-6
• 化学式: C₂₂H₃₆O₅Si
• 分子量: 408.61
• InChiKey: XLDNSLFBFUHQRO-QLUKVCKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid 在 4-二甲氨基吡啶 、 Hoveyda-Grubbs catalyst second generation 、 四氯化钛 、 对甲苯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.5h， 生成 (3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione
  参考文献：
  名称：

  Stereoselective total synthesis of clonostachydiol

  摘要：

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.014
• 作为产物：
  描述：

  (3R)-3-(tert-butyldimethylsilyloxy)butanal 在 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 nickel(II) chloride hexahydrate 、 lithium hydroxide monohydrate 、 二异丁基氢化铝 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 L-脯氨酸 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 27.0h， 生成 (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid
  参考文献：
  名称：

  Stereoselective total synthesis of clonostachydiol

  摘要：

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.014

文献信息

• Stereoselective total synthesis of (−)-(5S,8R,13S,16R)-pyrenophorol
  作者：Perugu Edukondalu、Reddymasu Sreenivasulu、Barreddi Chiranjeevi、Vuppula Naresh Kumar、Rudraraju Ramesh Raju

  DOI：10.1007/s00706-014-1406-3

  日期：2015.8

  AbstractThe total synthesis of 16-membered C 2-symmetric dilactone (−)-(5S,8R,13S,16R)-pyrenophorol was accomplished starting from enantiomerically pure propylene oxide prepared by hydrolytic kinetic resolution of (±)-propylene oxide with key steps of cross-metathesis and intermolecular Mitsunobu cyclization for the construction of macrolactone. Graphical abstract

  摘要从对映体纯的环氧丙烷（通过（±）-丙烯的水解动力学拆分制得）开始完成16元C 2对称双内酯（-）-（5 S，8 R，13 S，16 R）-pyrenophorol的全合成具有跨复分解和分子间光延环化关键步骤的环氧乙烷用于大内酯的构建。 图形概要
• Stereoselective total synthesis of clonostachydiol
  作者：Udugu Ramulu、Dasari Ramesh、Singanaboina Rajaram、Sudina Purushotham Reddy、Kunuru Venkatesham、Yenamandra Venkateswarlu

  DOI：10.1016/j.tetasy.2012.01.014

  日期：2012.1

  A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan alpha-hydroxylation, Horner-Wadsworth-Emmons (HWE) olefination, a Grignard reaction, and Hoveyda-Grubbs IInd generation catalyzed ring closing metathesis (RCM). (C) 2012 Elsevier Ltd. All rights reserved.