3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide | 875439-61-5

• 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: 3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide
• 英文别名: tert-butyl N-[3-(bromomethyl)-5-[tert-butyl(diphenyl)silyl]oxyphenyl]carbamate
• CAS: 875439-61-5
• 化学式: C₂₈H₃₄BrNO₃Si
• 分子量: 540.572
• InChiKey: JXUIFEXMEMURSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide 、 trivinylindium 在 Pd(diphenylphosphinoferrocene)Cl₂ 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以73%的产率得到
  参考文献：
  名称：

  Total Syntheses of New Proansamitocin Derivatives by Ring-Closing Metathesis

  摘要：

  描述了两种新的原安丝菌素衍生物的对映选择性合成。大环化是通过适当的烯烃和二烯前体的闭环复分解来实现的。

  DOI：

  10.1055/s-2007-977441
• 作为产物：
  描述：

  3-氨基-5-羟基苯甲酸甲酯 在 咪唑 、 4-二甲氨基吡啶 、 四溴化碳 、 二异丁基氢化铝 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.5h， 生成 3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q

文献信息

• Chemoenzymatic Approaches toward Dechloroansamitocin P-3
  作者：Axel Meyer、Marco Brünjes、Florian Taft、Thomas Frenzel、Florenz Sasse、Andreas Kirschning

  DOI：10.1021/ol0702270

  日期：2007.4.1

  The enantioselective total synthesis of proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin P-3, is described which bears a diene-ene RCM as the key macrocyclization step. Feeding of proansamitocin to an AHBA block mutant Actinosynnema pretiosum (HGF073) yielded ansamitocin P-3 as well as dechloroansamitocin P-3, the latter also being formed upon fermentation in the presence of 3-amino-5-methoxybenzoic acid.
• Total Syntheses of New Proansamitocin Derivatives by Ring-Closing Metathesis
  作者：Andreas Kirschning、Axel Meyer

  DOI：10.1055/s-2007-977441

  日期：——

  The enantioselective synthesis of two new proansamitocin derivatives is described. Macrocyclization is achieved by ring-closing metathesis of appropriate alkene and diene precursors.

  描述了两种新的原安丝菌素衍生物的对映选择性合成。大环化是通过适当的烯烃和二烯前体的闭环复分解来实现的。
• Synthesis of the <i>N</i>-Acetylcysteamine Thioester of <i>s</i><i>eco</i>-Proansamitocin
  作者：Thomas Frenzel、Marco Brünjes、Monika Quitschalle、Andreas Kirschning

  DOI：10.1021/ol052588q

  日期：2006.1.1

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.