(3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12-pentamethyl-5-oxo-tridec-12-enoic acid (1S,2S)-2-methyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester | 681259-83-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12-pentamethyl-5-oxo-tridec-12-enoic acid (1S,2S)-2-methyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester
• 英文别名: [(1E,3S,4S)-2,4-dimethyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-yl] (3S,6R,7S,8S)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8,12-pentamethyl-5-oxotridec-12-enoate
• CAS: 681259-83-6
• 化学式: C₄₂H₇₅NO₅SSi₂
• 分子量: 762.298
• InChiKey: AAWLRFFFSZNTLA-QYESPMJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.37
• 重原子数：
  51
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 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)-4,4,6,8,12-pentamethyl-5-oxo-tridec-12-enoic acid (1S,2S)-2-methyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 120.0h， 生成 (S)-14-methyl-epothilone D
  参考文献：
  名称：

  Rapid access to epothilone analogs via semisynthetic degradation and reconstruction of epothilone D

  摘要：

  A facile and efficient route to epothilone analogs has been developed from the natural product epothilone D (1). Degradation of 1 via an oxidative cleavage sequence provides acid intermediate 4 rapidly in six steps. From 4, a variety of epothilone analogs have been prepared utilizing ring-closing metathesis to reconstruct the trisubstituted-12,13-double bond. Using this approach, we report a number of epothilone analogs with varying C-15 aromatic side chains and C-14 allylic substitutions and their biological activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.123
• 作为产物：
  描述：

  埃博霉素 在 lead(IV) acetate 、 4-二甲氨基吡啶 、 lithium hydroxide 、 四氧化锇 、 四甲基乙二胺 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 、 苯 为溶剂， 生成 (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12-pentamethyl-5-oxo-tridec-12-enoic acid (1S,2S)-2-methyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester
  参考文献：
  名称：

  Rapid access to epothilone analogs via semisynthetic degradation and reconstruction of epothilone D

  摘要：

  A facile and efficient route to epothilone analogs has been developed from the natural product epothilone D (1). Degradation of 1 via an oxidative cleavage sequence provides acid intermediate 4 rapidly in six steps. From 4, a variety of epothilone analogs have been prepared utilizing ring-closing metathesis to reconstruct the trisubstituted-12,13-double bond. Using this approach, we report a number of epothilone analogs with varying C-15 aromatic side chains and C-14 allylic substitutions and their biological activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.123

文献信息

• Rapid access to epothilone analogs via semisynthetic degradation and reconstruction of epothilone D
  作者：Steven D. Dong、Kurt Sundermann、Karen M.J. Smith、Joseph Petryka、Fenghua Liu、David C. Myles

  DOI：10.1016/j.tetlet.2003.12.123

  日期：2004.2

  A facile and efficient route to epothilone analogs has been developed from the natural product epothilone D (1). Degradation of 1 via an oxidative cleavage sequence provides acid intermediate 4 rapidly in six steps. From 4, a variety of epothilone analogs have been prepared utilizing ring-closing metathesis to reconstruct the trisubstituted-12,13-double bond. Using this approach, we report a number of epothilone analogs with varying C-15 aromatic side chains and C-14 allylic substitutions and their biological activities. (C) 2004 Elsevier Ltd. All rights reserved.