(S)-methyl 3-((2S,3R,4S,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-phenyl-tetrahydrofuran-2-yl)-3-hydroxypropanoate | 1215285-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-methyl 3-((2S,3R,4S,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-phenyl-tetrahydrofuran-2-yl)-3-hydroxypropanoate
• 英文别名: (S)-methyl 3-((2S,3R,4S,5S)-3,4-bis(tertbutyldimethylsilyloxy)-5-phenyl-tetrahydrofuran-2-yl)-3-hydroxypropanoate
• CAS: 1215285-91-8
• 化学式: C₂₆H₄₆O₆Si₂
• 分子量: 510.819
• InChiKey: JXTUAZGPHPZTBE-NHFPKVKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 3-((2S,3R,4S,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-phenyl-tetrahydrofuran-2-yl)-3-hydroxypropanoate 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到(S)-methyl 3-((2S,3S,4R,5S)-3,4-dihydroxy-5-phenyltetrahydrofuran-2-yl)-3-hydroxypropanoate
  参考文献：
  名称：

  Apoptotic activities in closely related styryllactone stereoisomers toward human tumor cell lines: Investigation of synergism of styryllactone-induced apoptosis with TRAIL

  摘要：

  A related series of styryllactones with small functional and stereochemical variations were compiled for a comparative study of their apoptotic activities toward two tumorigenic and one non-tumorigenic control cell line. While a substantial range of intrinsic activity was observed, the relative order of activity of the different compounds toward the cell types varied somewhat as did the relative ratios of apoptosis and necrosis observed in conjunction with the loss of cell viability. While some of the styryllactones showed substantial activity, a small but significant apoptosis-induced synergism was demonstrated with (-)-altholactone and TRAIL (tumor necrosis factor-related apoptosis-inducing ligand). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.045
• 作为产物：
  描述：

  乙酸甲酯 、 (2R,3R,4S,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-phenyltetrahydrofuran-2-carbaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(S)-methyl 3-((2S,3R,4S,5S)-3,4-bis(tert-butyldimethylsilyloxy)-5-phenyl-tetrahydrofuran-2-yl)-3-hydroxypropanoate
  参考文献：
  名称：

  Apoptotic activities in closely related styryllactone stereoisomers toward human tumor cell lines: Investigation of synergism of styryllactone-induced apoptosis with TRAIL

  摘要：

  A related series of styryllactones with small functional and stereochemical variations were compiled for a comparative study of their apoptotic activities toward two tumorigenic and one non-tumorigenic control cell line. While a substantial range of intrinsic activity was observed, the relative order of activity of the different compounds toward the cell types varied somewhat as did the relative ratios of apoptosis and necrosis observed in conjunction with the loss of cell viability. While some of the styryllactones showed substantial activity, a small but significant apoptosis-induced synergism was demonstrated with (-)-altholactone and TRAIL (tumor necrosis factor-related apoptosis-inducing ligand). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.045