L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-2,4-di-O-mesyl-chiro-inositol | 200272-87-3

• 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: L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-2,4-di-O-mesyl-chiro-inositol
• CAS: 200272-87-3
• 化学式: C₂₁H₃₀O₉S₂
• 分子量: 490.596
• InChiKey: MLFWRPPRGOSZSG-LJDSDSDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  cesium acetate 、 L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-2,4-di-O-mesyl-chiro-inositol 在 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到D-5-O-acetyl-4-O-benzyl-2,3-O-cyclohexylidene-1,6-ene-myo-inositol
  参考文献：
  名称：

  Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

  摘要：

  The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6-deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10101-6
• 作为产物：
  描述：

  环己酮二甲缩酮 在 吡啶 、 四氯化碳 、 氢氧化钾 、 硫酸 、 苄基三乙基氯化铵 、 苄基三甲基氯化铵 、 lithium tri-t-butoxyaluminum hydride 、 硫脲 、 三苯基膦 、 cesium fluoride 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.17h， 生成 L-1-O-benzyl-5,6-O-cyclohexylidene-3-deoxy-2,4-di-O-mesyl-chiro-inositol
  参考文献：
  名称：

  Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

  摘要：

  The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6-deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10101-6