1D-3,4,5-O-tribenzoyl-myo-inositol | 142630-99-7

• 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: 1D-3,4,5-O-tribenzoyl-myo-inositol
• 英文别名: L-1,5,6-tri-O-benzoyl-myo-inositol
• CAS: 142630-99-7
• 化学式: C₂₇H₂₄O₉
• 分子量: 492.482
• InChiKey: DYZQMGLMEDWROY-WMGXJHCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  139.59
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1D-3,4,5-O-tribenzoyl-myo-inositol 在 lithium hydroxide 、 三甲基溴硅烷 、 sodium phosphate buffer 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 肌醇 1,2,6-三磷酸酯
  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：

  L-1,6-di-O-benzoyl-myo-inositol 在 吡啶 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1D-3,4,5-O-tribenzoyl-myo-inositol
  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

• Efficient and systematic syntheses of enantiomerically pure and regiospecifically protected myo-inositols
  作者：Karol S. Bruzik、Ming Daw Tsai

  DOI：10.1021/ja00042a011

  日期：1992.7

  Efficient and systematic syntheses of a variety of enantiomerically pure and regiospecifically protected myo-inositols, which can be readily used as precursors for most natural and unnatural derivatives of myo-inositol, have been developed. The key strategies are the use of camphor as a protecting group and a chiral auxiliary and the development of regiospecific control in various steps. The diastereomerically

  各种对映体纯的和区域特异性保护的肌醇的有效和系统合成已经开发出来，这些肌醇可以很容易地用作大多数天然和非天然肌醇衍生物的前体。关键策略是使用樟脑作为保护基团和手性助剂，并在各个步骤中进行区域特异性控制。非对映体纯 1 ~-2,3-O(l'R,2'R,4'R-1',7',7'-trimethyl(2.2.1) bicyclohept-2'-ylidene)-myo-inositol (la)通过用D-樟脑二甲基乙缩醛使肌醇缩醛化然后从甲醇中结晶以3 1%的产率获得。在路线 A 中，四醇 1a 与叔丁基二苯基甲硅烷基氯 (TBDPS-C1) 的甲硅烷基化仅提供 1-OTBDPS-4,5,6-三醇 7，其充当关键中间体。其他试剂的进一步保护，彻底或区域特异性，结合选择性脱保护步骤，导致受保护的肌醇在 1-, 5-, 6-, 1,4-, 43-, 5,6-, 1, 4,5-和 1,4,6-位。在路线
• General synthesis of phosphatidylinositol 3-phosphates
  作者：Karol S. Bruzik、Robert J. Kubiak

  DOI：10.1016/0040-4039(95)00317-6

  日期：1995.4

  Uniform synthetic approach to phosphatidylinositol 3-phosphate, 3,4-bisphosphate and 3,4,5-trisphosphate has been elaborated starting from 1D-1-O-tert-butyldiphenylsilyl- and 1,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-myo-inositols using regioselective benzoylation at the 3-, 3,4- and 3,4,5-positions of inositol.

  从1D-1- O-叔丁基二苯基甲硅烷基-和1,6- O-（1,1,3 ，3-四异丙基-1,3-二基） -肌醇-inositols使用区域选择性苯甲酰在3-，3,4-和肌醇3,4,5-位置。