(1R,2R,5S,5'S)-1,4,4,5'-tetramethyl-5'-[(2S,5R)-5-[(1S,2S,2'R,5R)-1,2',4,4-tetramethylspiro[3,8-dioxabicyclo[3.2.1]octane-2,5'-oxolane]-2'-yl]oxolan-2-yl]spiro[3,8-dioxabicyclo[3.2.1]octane-2,2'-oxolane] | 1259224-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2R,5S,5'S)-1,4,4,5'-tetramethyl-5'-[(2S,5R)-5-[(1S,2S,2'R,5R)-1,2',4,4-tetramethylspiro[3,8-dioxabicyclo[3.2.1]octane-2,5'-oxolane]-2'-yl]oxolan-2-yl]spiro[3,8-dioxabicyclo[3.2.1]octane-2,2'-oxolane]
• CAS: 1259224-63-9
• 化学式: C₃₀H₄₈O₇
• 分子量: 520.707
• InChiKey: MWUCLXVBYAZMCJ-CCOJBMFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  角鲨烯 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 以2.3%的产率得到(1R,2R,5S,5'S)-1,4,4,5'-tetramethyl-5'-[(2S,5S)-5-[(1R,2R,2'S,5S)-1,2',4,4-tetramethylspiro[3,8-dioxabicyclo[3.2.1]octane-2,5'-oxolane]-2'-yl]oxolan-2-yl]spiro[3,8-dioxabicyclo[3.2.1]octane-2,2'-oxolane]
  参考文献：
  名称：

  Discovery of a novel one-step RuO4-catalysed tandem oxidative polycyclization/double spiroketalization process. Access to a new type of polyether bis-spiroketal compound displaying antitumour activity

  摘要：

  Four novel C-30 polyether bis-spiroketals, displaying selective inhibition of the BT474 breast-derived cancer cell line, have been obtained from squalene through an unprecedented one-step, RuO4-catalysed, cascade process characterised by a tandem oxidative pentacyclization/double oxidative spiroketalization sequence. Preliminary studies indicate that the Ru-mediated spiroketalization steps proceed with retention of configuration at the forming spirocentres. A similarity with the oxidative behaviour of PCC has been disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.004