(10E,13Z)-(4S,7R,8S,9S,16S)-16-(2-Bromo-acetyl)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-oxacyclohexadeca-10,13-diene-2,6-dione | 905288-21-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (10E,13Z)-(4S,7R,8S,9S,16S)-16-(2-Bromo-acetyl)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-oxacyclohexadeca-10,13-diene-2,6-dione
• 英文别名: (4S,7R,8S,9S,10E,13Z,16S)-16-(2-bromoacetyl)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-5,5,7,9,13-pentamethyl-1-oxacyclohexadeca-10,13-diene-2,6-dione
• CAS: 905288-21-3
• 化学式: C₃₄H₆₁BrO₆Si₂
• 分子量: 701.93
• InChiKey: KUIQWUDXLXSKQJ-NWHRCBDPSA-N

物化性质

• 沸点：
  654.7±55.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (10E,13Z)-(4S,7R,8S,9S,16S)-16-(2-Bromo-acetyl)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-oxacyclohexadeca-10,13-diene-2,6-dione 在 4 A molecular sieve 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 15-(2-(2-methylthiazol-4-yl)thiazol-4-yl)-9,10-didehydroepothilone D
  参考文献：
  名称：

  C-15 Thiazol-4-yl Analogues of (E)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity

  摘要：

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.

  DOI：

  10.1021/ol061087h
• 作为产物：
  描述：

  (10E,13Z)-(4S,7R,8S,9S,16S)-16-acetyl-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-oxacyclohexadeca-10,13-diene-2,6-dione 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (10E,13Z)-(4S,7R,8S,9S,16S)-16-(2-Bromo-acetyl)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-oxacyclohexadeca-10,13-diene-2,6-dione
  参考文献：
  名称：

  C-15 Thiazol-4-yl Analogues of (E)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity

  摘要：

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.

  DOI：

  10.1021/ol061087h

文献信息

• C-15 Thiazol-4-yl Analogues of (<i>E</i>)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity
  作者：Brian R. Hearn、Dan Zhang、Yong Li、David C. Myles

  DOI：10.1021/ol061087h

  日期：2006.7.1

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.