tert-butyl (1R,2S,5E,7R,9R)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-7,9-dimethylundec-5-enyl]methylcarbamate | 1159216-09-7

• 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: tert-butyl (1R,2S,5E,7R,9R)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-7,9-dimethylundec-5-enyl]methylcarbamate
• CAS: 1159216-09-7
• 化学式: C₃₄H₆₁NO₅Si
• 分子量: 591.948
• InChiKey: PFSBQJIFNRQTQB-UHJIUPHJSA-N

物化性质

• 沸点：
  601.9±55.0 °C(predicted)
• 密度：
  0.965±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  41.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2S,5E,7R,9R)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-7,9-dimethylundec-5-enyl]methylcarbamate 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以89%的产率得到(2R,3S,6E,8R,10R)-1-(4-hydroxyphenyl)-8,10-dimethyl-2-(methylamino)dodec-6-en-3-ol
  参考文献：
  名称：

  Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells

  摘要：

  Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1 -dependent cancer cells, was succeeded by one-pot Julia Coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.003
• 作为产物：
  描述：

  tert-butyl (1R,2S)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-5-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]pentyl]methylcarbamate 、 (2R,4R)-2,4-dimethylhexanal 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.03h， 以56%的产率得到tert-butyl (1R,2S,5E,7R,9R)-[2-(tert-butyldimethylsilyloxy)-1-[4-(methoxymethoxy)benzyl]-7,9-dimethylundec-5-enyl]methylcarbamate
  参考文献：
  名称：

  Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells

  摘要：

  Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1 -dependent cancer cells, was succeeded by one-pot Julia Coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.003