(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-dec-9-enoic acid (Z)-(S)-4-methyl-1-(2-methyl-thiazol-4-yl)-hepta-3,6-dienyl ester | 905288-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-dec-9-enoic acid (Z)-(S)-4-methyl-1-(2-methyl-thiazol-4-yl)-hepta-3,6-dienyl ester
• 英文别名: [(1S,3Z)-4-methyl-1-(2-methyl-1,3-thiazol-4-yl)hepta-3,6-dienyl] (3S,6R,7S,8S)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxodec-9-enoate
• CAS: 905288-19-9
• 化学式: C₃₈H₆₇NO₅SSi₂
• 分子量: 706.191
• InChiKey: PJDBIXKJNXDJPK-FCWNRHPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.17
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-dec-9-enoic acid (Z)-(S)-4-methyl-1-(2-methyl-thiazol-4-yl)-hepta-3,6-dienyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以66%的产率得到(10E,13Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-(2-methyl-thiazol-4-yl)-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
• 作为产物：
  描述：

  (5,Z)-3-((tert-butyl)dimethylsiloxy)-6-methylnona-5,8-dien-2-one 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 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 乙醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-dec-9-enoic acid (Z)-(S)-4-methyl-1-(2-methyl-thiazol-4-yl)-hepta-3,6-dienyl ester
  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.