methyl 6-bromo-3,4-O-cyclohexylidene-6-deoxy-β-D-galactopyranoside | 156593-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-bromo-3,4-O-cyclohexylidene-6-deoxy-β-D-galactopyranoside
• CAS: 156593-31-6
• 化学式: C₁₃H₂₁BrO₅
• 分子量: 337.211
• InChiKey: WDQBENFRZAQULG-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-3,4-O-cyclohexylidene-6-deoxy-β-D-galactopyranoside 在 氢氧化钾 、 苄基三甲基氯化铵 、 sodium hydride 、 溶剂黄146 、 lithium tri-t-butoxyaluminum hydride 、 硫脲 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 L-2,4-di-O-benzoyl-1-O-benzyl-3-deoxy-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
• 作为产物：
  描述：

  环己酮二甲缩酮 在 吡啶 、 四溴化碳 、 硫酸 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl 6-bromo-3,4-O-cyclohexylidene-6-deoxy-β-D-galactopyranoside
  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