(2S,3RS,4RS)-4-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyl-oxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-2-methyl-5-oxotetrahydrofuran-3-yl acetate | 1262843-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3RS,4RS)-4-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyl-oxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-2-methyl-5-oxotetrahydrofuran-3-yl acetate
• CAS: 1262843-02-6
• 化学式: C₄₉H₉₆O₇Si₂
• 分子量: 853.468
• InChiKey: BXNKIMRNZDSHLQ-MWNKPXEKSA-N

反应信息

• 作为反应物：
  描述：

  (2S,3RS,4RS)-4-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyl-oxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-2-methyl-5-oxotetrahydrofuran-3-yl acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以100%的产率得到(5S)-3-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyloxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-5-methylfuran-2(5H)-one
  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：

  (3RS,4RS,5S)-3-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyloxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-4-hydroxy-5-methyldihydrofuran-2(3H)-one 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 以90%的产率得到(2S,3RS,4RS)-4-((13R)-13-(tert-butyldimethylsilyloxy)-13-{(2R,5R)-5-[(1R)-1-(tert-butyldimethylsilyl-oxy)tridecyl]tetrahydrofuran-2-yl}tridecyl)-2-methyl-5-oxotetrahydrofuran-3-yl acetate
  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