(2R)-(2,3/4)-2,3-dihydroxy-4-benzyloxy-2,3-O-cyclohexylidenecyclohexanone | 200273-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-(2,3/4)-2,3-dihydroxy-4-benzyloxy-2,3-O-cyclohexylidenecyclohexanone
• CAS: 200273-01-4
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: JDMDDDYOWLFSLY-GDPRMGEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R)-(2,3/4)-2,3-dihydroxy-4-benzyloxy-2,3-O-cyclohexylidenecyclohexanone 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到D-2,3-O-cyclohexylidene-5,6-dideoxy-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 palladium hydroxide - carbon 吡啶 、 四氯化碳 、 氢氧化钾 、 偶氮二甲酸二异丙酯 、 硫酸 、 氢气 、 苄基三甲基氯化铵 、 sodium hydride 、 硫脲 、 三苯基膦 、 苯甲酸 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~110.0 ℃ 、34.48 kPa 条件下， 反应 45.17h， 生成 (2R)-(2,3/4)-2,3-dihydroxy-4-benzyloxy-2,3-O-cyclohexylidenecyclohexanone
  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