(5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one | 190380-57-5

• 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: (5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one
• CAS: 190380-57-5
• 化学式: C₂₅H₄₈O₄Si
• 分子量: 440.739
• InChiKey: VLGLLLHWRYZJHL-MLCQCVOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one 在 palladium on activated charcoal Cl⁽³⁾HO₄ 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 (2S,2'S,5'S,2''S,5''S)-5''-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-dodecahydro-[2,2';5',2'']terfuran-5-ol
  参考文献：
  名称：

  Replicative Chirons:  Stereoselective Synthesis of Oligo-Tetrahydrofuranic Lactones via C-Glycosylation with [(Trimethylsilyl)oxy]furan

  摘要：

  DOI：

  10.1021/jo970212n
• 作为产物：
  描述：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 Cl⁽³⁾HO₄ 、 氢气 、 L-Selectride 、 二异丁基氢化铝 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 64.75h， 生成 (5S)-5-[(2S,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]oxolan-2-one
  参考文献：
  名称：

  Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues

  摘要：

  A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. Indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.

  DOI：

  10.1016/s0223-5234(97)83287-4

文献信息

• Stereocontrolled synthesis of key intermediates in the total synthesis of acetogenins of annonaceae
  作者：Bruno Figadère、Christophe Chaboche、Jean-François Peyrat、André Cavé

  DOI：10.1016/s0040-4039(00)61460-0

  日期：1993.12

  (4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid. The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation

  （4S，5S，8S，9S）-和（4R，5S，8S，9S）-9-羟基-5,8-环氧-丁香醇3b和4b已分别由非常便宜的L-谷氨酸成功合成。合成序列的关键步骤是将乙酸内酯乙酸酯5a，b与2-（三甲基甲硅烷氧基）-呋喃进行烷基化。从NMR数据和通过化学相关推导获得的产物的立体化学关系分配。
• Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues
  作者：A Cavé、C Chaboche、B Figadère、J.C. Harmange、A Laurens、J.F. Peyrat、M Pichon、M Szlosek、J Cotte-Lafitte、A.M. Quéro

  DOI：10.1016/s0223-5234(97)83287-4

  日期：1997.7

  A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. Indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.
• Replicative Chirons:  Stereoselective Synthesis of Oligo-Tetrahydrofuranic Lactones <i>via</i> C-Glycosylation with [(Trimethylsilyl)oxy]furan
  作者：Bruno Figadère、Jean-François Peyrat、André Cavé

  DOI：10.1021/jo970212n

  日期：1997.5.1