methyl (15R)-15-{(2R,5R)-5-[(1R)-1,10-bis(tert-butyldimethylsilyloxy)decyl]tetrahydrofuran-2-yl}-15-(tert-butyldimethylsilyloxy)pentadec-13-ynoate | 1006619-75-5

• 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: methyl (15R)-15-{(2R,5R)-5-[(1R)-1,10-bis(tert-butyldimethylsilyloxy)decyl]tetrahydrofuran-2-yl}-15-(tert-butyldimethylsilyloxy)pentadec-13-ynoate
• CAS: 1006619-75-5
• 化学式: C₄₈H₉₆O₆Si₃
• 分子量: 853.543
• InChiKey: BAOXINBIDSXKTI-OWIHLRRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.92
• 重原子数：
  57.0
• 可旋转键数：
  28.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (15R)-15-{(2R,5R)-5-[(1R)-1,10-bis(tert-butyldimethylsilyloxy)decyl]tetrahydrofuran-2-yl}-15-(tert-butyldimethylsilyloxy)pentadec-13-ynoate 、 (S)-2-(tetrahydropyranyloxy)propanal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 生成 methyl (15R)-15-((tert-butyldimethylsilyl)oxy)-2-((2S)-1-hydroxy-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-15-((2R,5R)-5-((R)-2,2,3,3,16,16,17,17-octamethyl-4,15-dioxa-3,16-disilaoctadecan-5-yl)tetrahydrofuran-2-yl)pentadec-13-ynoate
  参考文献：
  名称：

  Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

  摘要：

  The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.004
• 作为产物：
  描述：

  methyl (15R)-15-{(2R,5R)-5-[(1R)-1,10-bis(tert-butyldimethylsilyloxy)decyl]tetrahydrofuran-2-yl}-15-hydroxypentadec-13-ynoate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 以96%的产率得到methyl (15R)-15-{(2R,5R)-5-[(1R)-1,10-bis(tert-butyldimethylsilyloxy)decyl]tetrahydrofuran-2-yl}-15-(tert-butyldimethylsilyloxy)pentadec-13-ynoate
  参考文献：
  名称：

  Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

  摘要：

  The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.004

文献信息

• Synthesis of Fluorescent Solamin for Visualization of Cell Distribution
  作者：Tetsuaki Tanaka、Naoyoshi Maezaki、Daisuke Urabe、Masahiro Yano、Hiroaki Tominaga、Takekuni Morioka、Naoto Kojima

  DOI：10.3987/com-07-s(u)1

  日期：——