L-2,3,5-tri-O-benzoyl-myo-inositol 1,4,6-tris(diethyl phosphate) | 454198-70-0

• 分子结构分类: 有机化合物
• 英文名称: L-2,3,5-tri-O-benzoyl-myo-inositol 1,4,6-tris(diethyl phosphate)
• 英文别名: [(1R,2S,3S,4S,5R,6S)-2,5-dibenzoyloxy-3,4,6-tris(diethoxyphosphoryloxy)cyclohexyl] benzoate
• CAS: 454198-70-0
• 化学式: C₃₉H₅₁O₁₈P₃
• 分子量: 900.744
• InChiKey: FRDVVMHJNBQIPK-ZOXPVIOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  60
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  L-2,3,5-tri-O-benzoyl-myo-inositol 1,4,6-tris(diethyl phosphate) 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Divergent Syntheses of All Possible Optically Active Regioisomers of myo-Inositol Tris- and Tetrakisphosphates

  摘要：

  Since the discovery Of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz(3)s and IBz(2)s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositoI and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz(3) and six enantiomeric pairs of IBz(2), respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.

  DOI：

  10.1021/jo0257694
• 作为产物：
  描述：

  3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 在 吡啶 、 甲醇 、 sodium phosphate buffer 、 水 、 双氧水 、 溶剂黄146 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 L-2,3,5-tri-O-benzoyl-myo-inositol 1,4,6-tris(diethyl phosphate)
  参考文献：
  名称：

  Divergent Syntheses of All Possible Optically Active Regioisomers of myo-Inositol Tris- and Tetrakisphosphates

  摘要：

  Since the discovery Of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz(3)s and IBz(2)s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositoI and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz(3) and six enantiomeric pairs of IBz(2), respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.

  DOI：

  10.1021/jo0257694

文献信息

• Practical divergent synthesis of all possible regioisomers of myo-inositol trisphosphates
  作者：Sung-Kee Chung、Young-Tae Chang、Kwang-Hoon Sohn

  DOI：10.1039/cc9960000163

  日期：——

  The synthesis of all possible 12 regioisomers of IP3, some of which are implicated as second messengers in cellular signalling, is accomplished from myo-inositol via its tribenzoate derivatives(IBz3) as the key intermediates.

  所有可能的12种IP3区域异构体的合成完成，其中一些在细胞信号传导中被认为是第二信使，合成过程是通过其三苯甲酸酯衍生物（IBz3）作为关键中间体，从肌醇出发。