1,3,4,5,6-penta-O-benzyl-2-C-methyl-myo-inositol | 1436434-45-5

• 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: 1,3,4,5,6-penta-O-benzyl-2-C-methyl-myo-inositol
• CAS: 1436434-45-5
• 化学式: C₄₂H₄₄O₆
• 分子量: 644.808
• InChiKey: MKRDZAVFTICOKK-KTKNPLNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,3,4,5,6-penta-O-benzyl-2-C-methyl-myo-inositol 在 吡啶 、 4-二甲氨基吡啶 、 20% palladium hydroxide-activated charcoal 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 38.0h， 生成 1,3,4,5,6-penta-O-acetyl-2-C-methyl-myo-inositol
  参考文献：
  名称：

  The orientation of the β-hydroxyl group controls the diastereoselectivity during the hydride reduction and Grignard reaction of inososes

  摘要：

  A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the beta-hydroxyl group (or its derivative). Presence of an axial beta-hydroxyl group generally results in the formation of relatively larger amount of the axial alcohol as a result of the reduction of the carbonyl group. The possible reasons for the observed differences in diastereoselectivity between the reactions of these isomeric epi- and scyllo-inososes have been discussed. The sequence of reactions reported here provides convenient access to C-allcylated inositols, such as iso-laminitol and iso-mytilitol as well as 2-O-methyl epi-inositol, an epimer of the naturally occurring ononitol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.081
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.92h， 生成 1,3,4,5,6-penta-O-benzyl-2-C-methyl-myo-inositol 、 1-C-methyl-2,3,4,5,6-penta-O-benzyl-scyllo-inositol
  参考文献：
  名称：

  The orientation of the β-hydroxyl group controls the diastereoselectivity during the hydride reduction and Grignard reaction of inososes

  摘要：

  A comparison of the results of the Grignard reaction and the hydride reduction of the carbonyl group of epi- and scyllo-inososes reveals that the extent of diastereoselectivity of these reactions is decided by the orientation of the beta-hydroxyl group (or its derivative). Presence of an axial beta-hydroxyl group generally results in the formation of relatively larger amount of the axial alcohol as a result of the reduction of the carbonyl group. The possible reasons for the observed differences in diastereoselectivity between the reactions of these isomeric epi- and scyllo-inososes have been discussed. The sequence of reactions reported here provides convenient access to C-allcylated inositols, such as iso-laminitol and iso-mytilitol as well as 2-O-methyl epi-inositol, an epimer of the naturally occurring ononitol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.081