[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester | 120964-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester
• CAS: 120964-43-4
• 化学式: C₃₃H₃₈O₈
• 分子量: 562.66
• InChiKey: UQWHMWAWYWWPSL-HQILGIKTSA-N

物化性质

• 沸点：
  676.7±55.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl 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
• 作为产物：
  描述：

  [(1S,3S,4S,6S,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-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