5-O-benzhydryl-2,4,6-tri-O-methyl-myo-inositol | 197631-39-3

• 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: 5-O-benzhydryl-2,4,6-tri-O-methyl-myo-inositol
• CAS: 197631-39-3
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: YVCGPQCNAWTECC-ZYDGMWIZSA-N

反应信息

• 作为反应物：
  描述：

  5-O-benzhydryl-2,4,6-tri-O-methyl-myo-inositol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 、 苯 为溶剂， 反应 9.0h， 生成 1,3-O-diacetyl-2,4,6-tri-O-methyl-myo-inositol
  参考文献：
  名称：

  Chelation-Assisted C−O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s)

  摘要：

  Reactions of ortho esters of myo-inositol 8 or 10 with 1-2 equiv of Grignard reagents in benzene-ether yield regio-and stereoselectively the corresponding ring opening products having a free hydroxy group at C-l. The regioselectivity is rationalized owing to the presence of the 2-methoxy group which will serve as an auxiliary to form a chelation complex 12 with magnesium. Inositol derivatives having two free hydroxy group at C-l and C-3 positions can be achieved from reactions of 6 or 8 with excess Grignard reagents or under more drastic conditions. The reaction of 8b with excess LiAlH4/AlCl3, on the other hand, yields the corresponding 1,5-diol 19.

  DOI：

  10.1021/jo970606e
• 作为产物：
  描述：

  phenylmagnesium bromide 、 2,4,6-tri-O-methyl-meso-D-myo-inositol-1,3,5-O-orthoformate 以 乙醚 、 苯 为溶剂， 反应 16.0h， 以60%的产率得到5-O-benzhydryl-2,4,6-tri-O-methyl-myo-inositol
  参考文献：
  名称：

  Chelation-Assisted C−O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s)

  摘要：

  Reactions of ortho esters of myo-inositol 8 or 10 with 1-2 equiv of Grignard reagents in benzene-ether yield regio-and stereoselectively the corresponding ring opening products having a free hydroxy group at C-l. The regioselectivity is rationalized owing to the presence of the 2-methoxy group which will serve as an auxiliary to form a chelation complex 12 with magnesium. Inositol derivatives having two free hydroxy group at C-l and C-3 positions can be achieved from reactions of 6 or 8 with excess Grignard reagents or under more drastic conditions. The reaction of 8b with excess LiAlH4/AlCl3, on the other hand, yields the corresponding 1,5-diol 19.

  DOI：

  10.1021/jo970606e