(1R,3S,4S,5R,6R,7R)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo<2.2.1>heptane-7-acetic Acid Ethyl Ester | 120927-61-9

• 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,7R)-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,7R)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.1]heptane-7-acetic Acid Ethyl Ester；[(1R,3S,4S,5R,6R,7R)-7-(2-ethoxy-2-oxoethyl)-3-methoxy-6-phenylmethoxy-2-oxabicyclo[2.2.1]heptan-5-yl] benzoate
• CAS: 120927-61-9
• 化学式: C₂₅H₂₈O₇
• 分子量: 440.493
• InChiKey: JYTILAGKIMCMLN-KHYMHBLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  甲醇 、 (1R,3S,4S,5R,6R,7R)-5-(Benzoyloxy)-6-(benzyloxy)-3-methoxy-2-oxabicyclo<2.2.1>heptane-7-acetic Acid Ethyl Ester 在 camphor-10-sulfonic acid 作用下， 反应 4.0h， 以95%的产率得到[(3aR,4S,5R,6R,6aR)-4-(dimethoxymethyl)-2-oxo-6-phenylmethoxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
  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
• 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