[(1R,3S,4S,5S,6R,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 | 120927-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,3S,4S,5S,6R,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: 120927-69-7
• 化学式: C₃₃H₃₈O₈
• 分子量: 562.66
• InChiKey: UQWHMWAWYWWPSL-RROQGOQRSA-N

反应信息

• 作为产物：
  描述：

  [(1S,3S,4S,6R,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 2.0h， 以23%的产率得到[(1R,3S,4S,5S,6R,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