(3-bromo-5-methoxy-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane | 1005390-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-bromo-5-methoxy-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane
• 英文别名: [3-Bromo-5-methoxy-4-(methoxymethoxy)phenyl]methoxy-tert-butyl-dimethylsilane
• CAS: 1005390-85-1
• 化学式: C₁₆H₂₇BrO₄Si
• 分子量: 391.377
• InChiKey: ZZXOJDVLIRIPDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-bromo-5-methoxy-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane 、 香叶基溴 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.5h， 以78%的产率得到(E)-tert-butyl((3-(3,7-dimethylocta-2,6-dien-1-yl)-5-methoxy-4-(methoxymethoxy)benzyl)oxy)dimethylsilane
  参考文献：
  名称：

  Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

  摘要：

  Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.086
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 [3-Bromo-5-methoxy-4-(methoxymethoxy)phenyl]methanol 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以99%的产率得到(3-bromo-5-methoxy-4-methoxymethoxy-benzyloxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation

  摘要：

  Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.086

文献信息

• Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization
  作者：Jeffrey D. Neighbors、Joseph J. Topczewski、Dale C. Swenson、David F. Wiemer

  DOI：10.1016/j.tetlet.2009.04.052

  日期：2009.7

  The cis-fused hexahydroxanthene system can be obtained through a cascade cyclization initiated by Lewis acid-mediated epoxide opening and terminated by reaction with a MOM-protected phenol. Only a single diastereomer of the product was obtained with stereochemistry verified by diffraction analysis. This demonstrates the viability of this approach to natural products containing the cis-fused hexahydroxanthene

  顺式稠合六氢氧杂蒽系统可以通过由路易斯酸介导的环氧化物开环引发并通过与MOM保护的苯酚反应终止的级联环化反应而获得。通过衍射分析证实的立体化学仅获得产物的单一非对映异构体。这证明了该方法对含有顺式融合的六氢氧杂蒽骨架的天然产物的可行性，并支持通过类似策略制备更复杂的靶标。
• Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation
  作者：Jeffrey D. Neighbors、Nolan R. Mente、Kelly D. Boss、Donald W. Zehnder、David F. Wiemer

  DOI：10.1016/j.tetlet.2007.11.086

  日期：2008.1

  Use of a Shi epoxidation for introduction of chirality in a key epoxide intermediate, together with revised protecting group tactics, has allowed an efficient synthesis of the hexahydroxanthene subunit common to the natural schweinfurthin F and the synthetic analogue 3-deoxyschweinfurthin B. (C) 2007 Elsevier Ltd. All rights reserved.