(1R,3S,4S,5R,6R,7S)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo<2.2.1>heptane-7-acetic Acid Ethyl Ester | 120964-38-7

• 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: (1R,3S,4S,5R,6R,7S)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo<2.2.1>heptane-7-acetic Acid Ethyl Ester
• 英文别名: (1R,3S,4S,5R,6R,7S)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.1]heptane-7-acetic Acid Ethyl Ester；[(1R,3S,4S,5R,6R,7S)-7-(2-ethoxy-2-oxoethyl)-3-methoxy-6-phenylmethoxy-2-oxabicyclo[2.2.1]heptan-5-yl] benzoate
• CAS: 120964-38-7
• 化学式: C₂₅H₂₈O₇
• 分子量: 440.493
• InChiKey: JYTILAGKIMCMLN-BESGAPRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以59%的产率得到(1R,3S,4S,5R,6R,7R)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo<2.2.1>heptane-7-acetic Acid Ethyl Ester
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033