1-Camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol | 140391-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-Camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol
• 英文别名: 1-(1-(S)-camphanyl)-2,3:4,5-dicyclohexylidene-D-myo-inositol
• CAS: 140391-26-0
• 化学式: C₂₈H₄₀O₉
• 分子量: 520.62
• InChiKey: OJDLBTMJEWQGFE-YMKLXQDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-Camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (+)-biscyclohexylammonium myo-inositol 4-phosphate
  参考文献：
  名称：

  A Simple Synthesis ofD-Myo-Inositol 4-Phosphate andD-Myo-Inositol 6-Phosphate

  摘要：

  A simple synthesis of the title compounds from myo-inositol is reported. The procedure involves the regioselective dibutyltin oxide-promoted acylation of racemic 1,2:5,6-dicyclohexylidene-myo-inositol (2) with 1-(S)-(-)-camphanyl chloride followed by chromatographic separation of the resulting diastereomers.

  DOI：

  10.1080/00397919408011303
• 作为产物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (+/-)-1,2:5,6-dicyclohexylidene-myo-inositol 在 二正丁基氧化锡 作用下， 生成 1-Camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol 、 31-(1-(S)-camphanyl)-1,2:4,5-dicyclohexylidene-D-myo-inositol
  参考文献：
  名称：

  A Simple Synthesis ofD-Myo-Inositol 4-Phosphate andD-Myo-Inositol 6-Phosphate

  摘要：

  A simple synthesis of the title compounds from myo-inositol is reported. The procedure involves the regioselective dibutyltin oxide-promoted acylation of racemic 1,2:5,6-dicyclohexylidene-myo-inositol (2) with 1-(S)-(-)-camphanyl chloride followed by chromatographic separation of the resulting diastereomers.

  DOI：

  10.1080/00397919408011303

文献信息

• Synthesis and characterization of an insulin-mimetic disaccharide
  作者：Robert Plourde、Marc D'Alarcao、Alan R. Saltiel

  DOI：10.1021/jo00035a015

  日期：1992.4

  A glucosaminyl-inositol-1,2-cyclic phosphate, 1, has been synthesized and evaluated for selected insulin-mimetic properties. The compound was designed to resemble structurally the recently reported inositol glycans which are believed to be insulin second messengers. The synthesis utilized a Koenigs-Knorr glycosylation of optically pure 1-camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol with 2-azido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide followed by phosphitylation by the phosphoramidite method, oxidation, and carbodiimide cyclization. Compound 1 was found to stimulate lipogenesis in rat adipocytes in a dose-dependent manner in the micromolar range up to a level 30-40% of that maximally induced by insulin.