1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate | 1309675-20-4

• 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: 1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate
• 英文别名: 1-O-benzyl 4-O-ethyl (2S)-2-[(1R,3R)-1-bis(prop-2-enoxy)phosphoryloxy-3-(2-chloroacetyl)oxy-5-trimethylsilylpent-4-ynyl]-2-[tert-butyl(dimethyl)silyl]oxybutanedioate
• CAS: 1309675-20-4
• 化学式: C₃₅H₅₄ClO₁₁PSi₂
• 分子量: 773.405
• InChiKey: REARNXUIKJVXHC-KQDQWFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  50
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-benzyl 4-ethyl (2S)-2-((tert-butyldimethylsilyl)oxy)-2-((1R,3S)-1,3-dihydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)succinate 在 四氮唑 、 叔丁基过氧化氢 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate
  参考文献：
  名称：

  Formal Synthesis of Leustroducsin B via Reformatsky/Claisen Condensation of Silyl Glyoxylates

  摘要：

  A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched beta-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishl's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).

  DOI：

  10.1021/ol2011192

文献信息

• Remote Stereoinduction in the Acylation of Fully Substituted Enolates: Tandem Reformatsky/Quaternary Claisen Condensations of Silyl Glyoxylates and β-Lactones
  作者：Stephen N. Greszler、Justin T. Malinowski、Jeffrey S. Johnson

  DOI：10.1021/ja108848d

  日期：2010.12.15

  glyoxylates and β-lactones to give highly functionalized Claisen condensation products. A heretofore undocumented instance of stereochemical 1,4-induction results in efficient transmission of β-lactone stereochemistry to the emerging fully substituted stereocenter. Second-stage transformations reveal that the five heteroatom-containing functionalities embedded within the products are entirely chemo-differentiated

  Reformatsky 试剂依次与乙醛酸甲硅烷基酯和 β-内酯反应，得到高度官能化的克莱森缩合产物。迄今为止未记录的立体化学 1,4-诱导实例导致 β-内酯立体化学有效传输到新兴的完全取代的立体中心。第二阶段的转化表明，嵌入产品中的五个含杂原子的功能是完全化学分化的，这种情况允许快速组装 leustroducsin B 核心亚结构。
• Formal Synthesis of Leustroducsin B via Reformatsky/Claisen Condensation of Silyl Glyoxylates
  作者：Stephen N. Greszler、Justin T. Malinowski、Jeffrey S. Johnson

  DOI：10.1021/ol2011192

  日期：2011.6.17

  A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched beta-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishl's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).