dimethyl [2-keto-(3R,4S,5R)-tri-O-benzyl-6(E),8-dienonon-1-yl]phosphonate | 1054614-20-8

• 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: dimethyl [2-keto-(3R,4S,5R)-tri-O-benzyl-6(E),8-dienonon-1-yl]phosphonate
• 英文别名: (3R,4S,5R,6E)-1-dimethoxyphosphoryl-3,4,5-tris(phenylmethoxy)nona-6,8-dien-2-one
• CAS: 1054614-20-8
• 化学式: C₃₂H₃₇O₇P
• 分子量: 564.615
• InChiKey: QYLWRVICOBFUDS-FCISXNMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl [2-keto-(3R,4S,5R)-tri-O-benzyl-6(E),8-dienonon-1-yl]phosphonate 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 (2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin
  参考文献：
  名称：

  Approach Towards Highly Oxygenated cis‐Decalins from Sugar Allyltins

  摘要：

  A convenient method for the preparation of sugar allyltin derivatives and their application in stereocontrolled synthesis of highly oxygenated, optically pure carbobicyclic derivatives is presented. Special attention is focused on stereoselective transformations of the precursors obtained directly from sugar allyltins.

  DOI：

  10.1080/07328300600732782
• 作为产物：
  描述：

  (2R,3S,4R,5E)-2,3,4-tribenzyloxyocta-5,7-diene-1-al 在 正丁基锂 、 jones' reagent 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 dimethyl [2-keto-(3R,4S,5R)-tri-O-benzyl-6(E),8-dienonon-1-yl]phosphonate
  参考文献：
  名称：

  Approach Towards Highly Oxygenated cis‐Decalins from Sugar Allyltins

  摘要：

  A convenient method for the preparation of sugar allyltin derivatives and their application in stereocontrolled synthesis of highly oxygenated, optically pure carbobicyclic derivatives is presented. Special attention is focused on stereoselective transformations of the precursors obtained directly from sugar allyltins.

  DOI：

  10.1080/07328300600732782

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。
• Approach Towards Highly Oxygenated <i>cis</i>‐Decalins from Sugar Allyltins
  作者：Sławomir Jarosz、Marcin Nowogródzki

  DOI：10.1080/07328300600732782

  日期：2006.5.1

  A convenient method for the preparation of sugar allyltin derivatives and their application in stereocontrolled synthesis of highly oxygenated, optically pure carbobicyclic derivatives is presented. Special attention is focused on stereoselective transformations of the precursors obtained directly from sugar allyltins.