(1S,2R,6R,8R,11R)-11-(diphenylphosphorylmethyl)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane | 1106973-97-0

• 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: (1S,2R,6R,8R,11R)-11-(diphenylphosphorylmethyl)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
• CAS: 1106973-97-0
• 化学式: C₂₂H₂₅O₆P
• 分子量: 416.411
• InChiKey: TXNOODFDNVFJQE-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,6R,8R,11R)-11-(diphenylphosphorylmethyl)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 1,2-O-异亚丙基-alpha-D-呋喃木糖
  参考文献：
  名称：

  Diphenylphosphinoylethylidene (DPE) acetals: an alternative protective strategy in glycochemistry

  摘要：

  Diphenylphoshinoylethyne reacts with diols under basic conditions to produce cycloacetalic phosphine oxides. The reaction appears to be general and particularly effective with carbohydrate derivatives. The 2-(diphenylplioshinoyl)ethylidene (DPE) acetals produced are stable in acidic media while they can be cleaved under reductive and/or basic conditions: base-catalyzed transacetalization is a method of choice for their mild and effective deprotection. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.10.111
• 作为产物：
  描述：

  [乙炔基(苯基)磷酰基]苯 、 1,2-O-异亚丙基-alpha-D-呋喃木糖 在 四丁基溴化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以75%的产率得到(1S,2R,6R,8R,11R)-11-(diphenylphosphorylmethyl)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
  参考文献：
  名称：

  Diphenylphosphinoylethylidene (DPE) acetals: an alternative protective strategy in glycochemistry

  摘要：

  Diphenylphoshinoylethyne reacts with diols under basic conditions to produce cycloacetalic phosphine oxides. The reaction appears to be general and particularly effective with carbohydrate derivatives. The 2-(diphenylplioshinoyl)ethylidene (DPE) acetals produced are stable in acidic media while they can be cleaved under reductive and/or basic conditions: base-catalyzed transacetalization is a method of choice for their mild and effective deprotection. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.10.111