(S)-2-ethoxy-1-((1S,2S,4R,6S)-4-ethoxy-5,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-yl)-2-oxoethyl 4-iodobenzoate | 1072923-96-6

• 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: (S)-2-ethoxy-1-((1S,2S,4R,6S)-4-ethoxy-5,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-yl)-2-oxoethyl 4-iodobenzoate
• CAS: 1072923-96-6
• 化学式: C₂₀H₂₅IO₇
• 分子量: 504.319
• InChiKey: XXQDNYODFHFIII-POORBHPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.59
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-碘苯甲酸 、 ethyl (R)-2-((1S,2R,4R,6S)-4-ethoxy-5,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-yl)-2-hydroxyacetate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以95%的产率得到(S)-2-ethoxy-1-((1S,2S,4R,6S)-4-ethoxy-5,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-2-yl)-2-oxoethyl 4-iodobenzoate
  参考文献：
  名称：

  Synthetic studies toward the pyran core and the amide side chain of psymberin

  摘要：

  A synthetic approach to the polysubstituted pyran core and amide side chain of psymberin (irciniastatin A) using stereoselective organoboron methodology is described. An advanced oxyranyl pyran intermediate was prepared using a catalytic enantioselective and diastereoselective three-component reaction involving first an inverse electron-demand hetero [4+2] cycloaddition between 3-boronoacrolein pinacolate and 1-ethoxy-2-methylpropene, followed by an allylboration of ethyl glyoxylate. The amide side chain was prepared highly efficiently using the first example of a doubly diastereoselective allylboration of a chiral alpha-alkoxy aldehyde under the Lewis acid-catalyzed reaction manifold. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.170