(2E,4E,6R,7S)-ethyl 7-(tert-butyldimethylsilyloxy)-7-((2R,3R)-3-((5R,10S,11S,E)-10-hydroxy-2,2,3,3,11,15,15,16,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-7-en-5-yl)oxiran-2-yl)-2,4,6-trimethylhepta-2,4-dienoate | 1415654-84-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E,6R,7S)-ethyl 7-(tert-butyldimethylsilyloxy)-7-((2R,3R)-3-((5R,10S,11S,E)-10-hydroxy-2,2,3,3,11,15,15,16,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-7-en-5-yl)oxiran-2-yl)-2,4,6-trimethylhepta-2,4-dienoate
• 英文别名: ethyl (2E,4E,6R,7S)-7-[(2R,3R)-3-[(E,1R,6S,7S)-1,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxy-7-methylnon-3-enyl]oxiran-2-yl]-7-[tert-butyl(dimethyl)silyl]oxy-2,4,6-trimethylhepta-2,4-dienoate
• CAS: 1415654-84-0
• 化学式: C₄₂H₈₂O₇Si₃
• 分子量: 783.365
• InChiKey: VNQHTBMHQTVKLM-AZFTWTTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.37
• 重原子数：
  52
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E,4E,6R,7S)-ethyl 7-(tert-butyldimethylsilyloxy)-7-((2R,3R)-3-((5R,10S,11S,E)-10-hydroxy-2,2,3,3,11,15,15,16,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-7-en-5-yl)oxiran-2-yl)-2,4,6-trimethylhepta-2,4-dienoate 在 potassium tert-butyldimethylsilanolate 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 51.0h， 生成 (1R,2R,4E,7S,10E,12E,14R,15S,16R)-2,15-bis(tert-butyldimethylsilyloxy)-7-((S)-4-(tert-butyldimethylsilyloxy)butan-2-yl)-10,12,14-trimethyl-8,17-dioxabicyclo[14.1.0]heptadeca-4,10,12-trien-9-one
  参考文献：
  名称：

  Stereoselective Total Synthesis of FD-891

  摘要：

  FD-891, a structurally unique 16-membered macrolide having anticancer activity, was synthesized according to a strategy employing asymmetric allylation, Prins cyclization, cross-metathesis reaction, Yamaguchi lactonization, and Julia-Kocienski olefination.

  DOI：

  10.1021/jo302205t
• 作为产物：
  描述：

  (2E,4E,6R,7S)-ethyl 7-(tert-butyldimethylsilyloxy)-7-((2R,3S)-3-((R)-1-hydroxybut-3-enyl)oxiran-2-yl)-2,4,6-trimethylhepta-2,4-dienoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2E,4E,6R,7S)-ethyl 7-(tert-butyldimethylsilyloxy)-7-((2R,3R)-3-((5R,10S,11S,E)-10-hydroxy-2,2,3,3,11,15,15,16,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-7-en-5-yl)oxiran-2-yl)-2,4,6-trimethylhepta-2,4-dienoate
  参考文献：
  名称：

  Stereoselective Total Synthesis of FD-891

  摘要：

  FD-891, a structurally unique 16-membered macrolide having anticancer activity, was synthesized according to a strategy employing asymmetric allylation, Prins cyclization, cross-metathesis reaction, Yamaguchi lactonization, and Julia-Kocienski olefination.

  DOI：

  10.1021/jo302205t

文献信息

• Stereoselective Total Synthesis of FD-891
  作者：J. S. Yadav、Sukant Kishore Das、G. Sabitha

  DOI：10.1021/jo302205t

  日期：2012.12.21

  FD-891, a structurally unique 16-membered macrolide having anticancer activity, was synthesized according to a strategy employing asymmetric allylation, Prins cyclization, cross-metathesis reaction, Yamaguchi lactonization, and Julia-Kocienski olefination.