bastadin 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: bastadin 3
• 英文别名: 3-[3-bromo-5-[3-bromo-5-[3-[2-(3-bromo-4-hydroxyphenyl)ethylamino]-2-hydroxyimino-3-oxopropyl]-2-hydroxyphenyl]-4-hydroxyphenyl]-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-2-hydroxyiminopropanamide
• 化学式: C₃₄H₃₀Br₄N₄O₈
• 分子量: 942.25
• InChiKey: XEGSWNKCRGYRFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  204
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-(2-amino-ethyl)-2-bromo-phenol; hydrochloride 在 茴香硫醚 、 三氟化硼 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 bastadin 3
  参考文献：
  名称：

  Total Synthesis of Bastadins 2, 3, and 6

  摘要：

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.

  DOI：

  10.1021/jo9721204

文献信息

• Total Synthesis of Bastadins 2, 3, and 6
  作者：Zhi-wei Guo、Koji Machiya、Grzegorz M. Salamonczyk、Charles J. Sih

  DOI：10.1021/jo9721204

  日期：1998.6.1

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.