(2S,3S,4R,5E)-2,3,4-tris(phenylmethoxy)octa-5,7-dienal | 193603-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R,5E)-2,3,4-tris(phenylmethoxy)octa-5,7-dienal
• CAS: 193603-90-6
• 化学式: C₂₉H₃₀O₄
• 分子量: 442.555
• InChiKey: LIXSPXSMHJXSFI-YXCPSXRPSA-N

物化性质

• 沸点：
  582.2±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (2S,3S,4R,5E)-2,3,4-tris(phenylmethoxy)octa-5,7-dienal 在 咪唑 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 paraffin 为溶剂， 反应 3.33h， 生成 2,3,4-tri-O-benzyl-5,6,7,8-tetradeoxy-5(E),7-dieno-oct-D-lyxitol xanthate
  参考文献：
  名称：

  Mach; Jarosz, Polish Journal of Chemistry, 1997, vol. 71, # 7, p. 936 - 940

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 在 zinc(II) chloride 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 生成 (2S,3S,4R,5E)-2,3,4-tris(phenylmethoxy)octa-5,7-dienal
  参考文献：
  名称：

  Kozlowska, Elzbieta; Jarosz, Slawomir, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 889 - 898

  摘要：

  DOI：

文献信息

• A convenient route to enantiomerically pure highly oxygenated decalins from sugar allyltin derivatives
  作者：Sławomir Jarosz、Stanisław Skóra

  DOI：10.1016/s0957-4166(00)00084-7

  日期：2000.4

  Preparation of enantiomerically pure, highly oxygenated decalins via tandem Wittig-type Diels–Alder reactions from the corresponding sugar-derived dieno-phosphoranes and/or -phosphonates and sugar aldehydes is described. Application of the phosphonates is more convenient than phosphoranes since the former can be prepared in much higher yields and react with aldehydes under milder conditions. The intermediate

  描述了通过串联的Wittig型Diels-Alder反应从相应的糖衍生的二膦基膦酸酯和/或-膦酸酯和糖醛制备对映体纯的，高度氧化的十氢化萘。膦酸酯的施用比磷烷更方便，因为前者可以更高的产率制备，并在温和的条件下与醛反应。在反应条件下，由Wittig-型方法产生的中间体三烯自发且高度立体选择性地环化为顺式-十氢化萘。
• Tandem Wittig–Diels–Alder reaction between sugar-derived phosphoranes and sugar aldehydes. An easy route to optically pure highly oxygenated decalins
  作者：Sławomir Jarosz

  DOI：10.1039/a707447f

  日期：——

  A highly oxygenated decalin system has been obtained by a tandem Wittig–Diels–Alder reaction of sugar derived phosphoranes with sugar aldehydes.

  通过糖源磷烯与糖醛的串联Wittig-Diels-Alder反应，获得了一种高度氧化的二氢萘系统。
• A convenient route to enantiomerically pure bicyclo[4.3.0]nonanes from sugar allyltin derivatives
  作者：Sławomir Jarosz、Stanisław Skóra

  DOI：10.1016/s0957-4166(00)00083-5

  日期：2000.4

  Tandem Wittig-type Diels-Alder reactions between sugar derived phosphonates and dienoaldehydes obtained from sugar allyltins lead, with high stereoselectivity, to complex oxygenated perhydroindene derivatives with the trans junction between the five- and six-membered rings. The configuration at the newly created stereogenic centers in such bicyclo[4.3.0] systems may be monitored by the geometry of chiral phosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Stability of regioisomeric sugar allyltins. Cleavage of the carbon oxygen bond under radical conditions
  作者：Sławomir Jarosz、Katarzyna Szewczyk

  DOI：10.1016/s0040-4039(01)00239-8

  日期：2001.4

  Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140 degreesC) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170 degreesC. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Kozlowska, Elzbieta; Jarosz, Slawomir, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 889 - 898
  作者：Kozlowska, Elzbieta、Jarosz, Slawomir

  DOI：——

  日期：——