3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzoic acid methyl ester | 875439-69-3

• 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)-benzoic acid methyl ester
• 英文别名: methyl 3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldiphenylsilyl)oxy]benzoate；Methyl 3-[tert-butyl(diphenyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate
• CAS: 875439-69-3
• 化学式: C₂₉H₃₅NO₅Si
• 分子量: 505.686
• InChiKey: INNBZBPYEQYFJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzoic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到methyl 3-amino-5-((tert-butyldiphenylsilyl)oxy)benzoate
  参考文献：
  名称：

  Bioreduction of Aryl Azides during Mutasynthesis of New Ansamitocins

  摘要：

  Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic acid, unexpectedly yielded anilino ansamitocins instead of the expected azido derivatives. This is the first example of the bioreduction of organic azides. The unique nature of these results was demonstrated when 3-azido-5-amino-benzoic acid was fed to the corresponding AHBA blocked mutant of Streptomyces hygroscopicus, the geldanamycin producer. This mutasynthetic experiment yielded the fully processed azido derivative of geldanamycin.

  DOI：

  10.1021/ol401989e
• 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 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzoic acid methyl ester
  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

• 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。