(2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde | 1002753-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde
• 英文别名: (2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-phenyloxolane-2-carbaldehyde
• CAS: 1002753-33-4
• 化学式: C₂₃H₄₀O₄Si₂
• 分子量: 436.739
• InChiKey: MGEAAMCEAAHYCF-DOIPELPJSA-N

物化性质

• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde 在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate
  参考文献：
  名称：

  高度立体选择性地合成抗肿瘤药：菊芋二醇，甲内酯和异甲内酯的对映异构体

  摘要：

  描述了从容易获得的肉桂醇合成高度官能化的取代的四氢呋喃的对映异构体和α，β-不饱和-δ-内酯，菊苣二醇，甲内酯和异甲内酯的对映体的灵活的立体选择性途径。这种方法的不对称性源于Sharpless催化不对称环氧化和Sharpless不对称二羟基化反应。所产生的二醇以高对映体过量产生，并在催化量的樟脑磺酸存在下以立体选择性方式环化。

  DOI：

  10.1016/j.tetasy.2005.08.047
• 作为产物：
  描述：

  ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3R,4R,5R)-tetrahydro-2-furancarboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde
  参考文献：
  名称：

  高度立体选择性地合成抗肿瘤药：菊芋二醇，甲内酯和异甲内酯的对映异构体

  摘要：

  描述了从容易获得的肉桂醇合成高度官能化的取代的四氢呋喃的对映异构体和α，β-不饱和-δ-内酯，菊苣二醇，甲内酯和异甲内酯的对映体的灵活的立体选择性途径。这种方法的不对称性源于Sharpless催化不对称环氧化和Sharpless不对称二羟基化反应。所产生的二醇以高对映体过量产生，并在催化量的樟脑磺酸存在下以立体选择性方式环化。

  DOI：

  10.1016/j.tetasy.2005.08.047

文献信息

• First Total Synthesis and Absolute Configuration of the Styryl Lactone Gonioheptolide A
  作者：Richard Hudson、Shuchi Gupta、Murali Rajagopalan、Mamoun Alhamadsheh、L. Tillekeratne

  DOI：10.1055/s-2007-990862

  日期：2007.11

  Efficient asymmetric syntheses of both naturally occurring and non-naturally occurring enantiomers of gonioheptolide A are reported. The absolute configuration of (+)-gonioheptolide A was established by NOESY, Mosher ester analysis, and comparison with the specific rotation of the isolated (+)-gonioheptolide A.

  报道了天然和非天然的戈尼庚醇A对映异构体的高效不对称合成。通过NOESY、Mosher酯分析以及与分离得到的(+)-戈尼庚醇A的特定旋光度进行比较，确立了(+)-戈尼庚醇A的绝对构型。
• Apoptotic activities in closely related styryllactone stereoisomers toward human tumor cell lines: Investigation of synergism of styryllactone-induced apoptosis with TRAIL
  作者：Shuchi Gupta、Lee Poeppelman、Channing. L. Hinman、James Bretz、Richard A. Hudson、L.M. Viranga Tillekeratne

  DOI：10.1016/j.bmc.2009.11.045

  日期：2010.1

  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.
• Highly stereoselective synthesis of antitumor agents: both enantiomers of goniothales diol, altholactone, and isoaltholactone
  作者：Jhillu Singh Yadav、Atcha Krishnam Raju、Ponugoti Purushothama Rao、Gurram Rajaiah

  DOI：10.1016/j.tetasy.2005.08.047

  日期：2005.10

  A flexible stereoselective route to synthesize both enantiomers of the highly functionalized substituted tetrahydrofurans and α,β-unsaturated-δ-lactones, goniothales diol, altholactone, and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The

  描述了从容易获得的肉桂醇合成高度官能化的取代的四氢呋喃的对映异构体和α，β-不饱和-δ-内酯，菊苣二醇，甲内酯和异甲内酯的对映体的灵活的立体选择性途径。这种方法的不对称性源于Sharpless催化不对称环氧化和Sharpless不对称二羟基化反应。所产生的二醇以高对映体过量产生，并在催化量的樟脑磺酸存在下以立体选择性方式环化。