(2-{3,5-Dibromo-4-[3-bromo-5-(2-{3-(3,5-dibromo-4-{9-bromo-3-[(Z)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-ethyl)-2-hydroxy-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester | 210880-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (2-{3,5-Dibromo-4-[3-bromo-5-(2-{3-(3,5-dibromo-4-{9-bromo-3-[(Z)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-ethyl)-2-hydroxy-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[3,5-dibromo-4-[3-bromo-5-[2-[[3-[3,5-dibromo-4-[(7-bromo-3-hydroxyimino-2,8-dioxo-1-oxaspiro[4.5]deca-6,9-dien-9-yl)oxy]phenyl]-2-hydroxyiminopropanoyl]amino]ethyl]-2-hydroxyphenoxy]phenyl]ethyl]carbamate
• CAS: 210880-83-4
• 化学式: C₃₉H₃₄Br₆N₄O₁₁
• 分子量: 1214.14
• InChiKey: LKCLVYXVGOGPGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.44
• 重原子数：
  60.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  214.67
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2-{3,5-Dibromo-4-[3-bromo-5-(2-{3-(3,5-dibromo-4-{9-bromo-3-[(Z)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-ethyl)-2-hydroxy-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester 在 sodium hydroxide 、 sodium hydrogensulfite 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 3-[3-(4-{2-(2-{3-[4-(2-Amino-ethyl)-2,6-dibromo-phenoxy]-5-bromo-4-hydroxy-phenyl}-ethylcarbamoyl)-2-[(E)-hydroxyimino]-ethyl}-2,6-dibromo-phenoxy)-5-bromo-4-hydroxy-phenyl]-2-[(Z)-hydroxyimino]-propionic acid
  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
• 作为产物：
  描述：

  N-Boc-3,5-dibromo-4-hydroxyphenethylamine 在 chromium dichloride 、 双氧水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 soybean peroxidase 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.83h， 生成 (2-{3,5-Dibromo-4-[3-bromo-5-(2-{3-(3,5-dibromo-4-{9-bromo-3-[(Z)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-ethyl)-2-hydroxy-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester
  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