2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazole-4-carbaldehyde | 1246973-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazole-4-carbaldehyde
• CAS: 1246973-15-8
• 化学式: C₂₇H₄₁NO₆Si
• 分子量: 503.711
• InChiKey: DLUONXAKESXJGH-ODXOUBHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazole-4-carbaldehyde 、 tributyl-[(Z,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyloct-2-en-6-ynyl]phosphanium;bromide 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以128 mg的产率得到tert-butyl-[(1E,3Z,5S,6R)-1-[2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazol-4-yl]-6-methylnona-1,3-dien-7-yn-5-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Total Synthesis of Chivosazole F

  摘要：

  The first synthesis of the highly biologically active chivosazole F is described. It features an intramolecular Stille coupling for the macrolactone formation and thereby circumvents the problem of isomerization associated with the tetraene segment. Additionally, the synthesis confirms the structure which has been proposed based solely on a combination of NMR/computational methods and genetic analysis.

  DOI：

  10.1021/ja107290s
• 作为产物：
  描述：

  methyl 2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazole-4-carboxylate 在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 二氯甲烷 、 甲苯 、 甲醇 为溶剂， 反应 3.0h， 以83%的产率得到2-[(E,2R,3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-8-[(4-methoxyphenyl)methoxy]oct-6-en-2-yl]-1,3-oxazole-4-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Chivosazole F

  摘要：

  The first synthesis of the highly biologically active chivosazole F is described. It features an intramolecular Stille coupling for the macrolactone formation and thereby circumvents the problem of isomerization associated with the tetraene segment. Additionally, the synthesis confirms the structure which has been proposed based solely on a combination of NMR/computational methods and genetic analysis.

  DOI：

  10.1021/ja107290s

文献信息

• Total Synthesis of Chivosazole F
  作者：Tobias Brodmann、Dominic Janssen、Markus Kalesse

  DOI：10.1021/ja107290s

  日期：2010.10.6

  The first synthesis of the highly biologically active chivosazole F is described. It features an intramolecular Stille coupling for the macrolactone formation and thereby circumvents the problem of isomerization associated with the tetraene segment. Additionally, the synthesis confirms the structure which has been proposed based solely on a combination of NMR/computational methods and genetic analysis.