D-2,4-di-O-benzoyl-myo-inositol | 455268-89-0

• 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: D-2,4-di-O-benzoyl-myo-inositol
• CAS: 455268-89-0
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: FULZFGPWFILVPE-PCCRXHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133.52
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 、 D-2,4-di-O-benzoyl-myo-inositol 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 C₇₆H₇₂O₁₆P₄
  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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 D-2,4-di-O-benzoyl-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

• Regioselectivity among six secondary hydroxyl groups: selective acylation of the least reactive hydroxyl groups of inositol
  作者：Amol M. Vibhute、Adiyala Vidyasagar、Saritha Sarala、Kana M. Sureshan

  DOI：10.1039/c2cc17241k

  日期：——

  We report the first, general and selective acylation of the least reactive hydroxyl group among six secondary hydroxyl groups of inositol in high yield, using very cheap and easy-to-make H(2)SO(4)-silica as the catalyst, providing easy access to bioactive molecules.

  我们报告的高收率，使用非常便宜和易于制造的H（2）SO（4）-二氧化硅作为催化剂，在肌醇的六个仲羟基中反应性最小的羟基的第一，通用和选择性的酰化作用，提供容易获得生物活性分子。
• Racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate: a versatile intermediate for the preparation of myo-inositol phosphates
  作者：Tanya Das、Mysore S Shashidhar

  DOI：10.1016/s0008-6215(98)00061-5

  日期：1998.3

  The versatility of racemic 2,4-di-O-benzoyl-myo-inositol 1,3,5-orthoformate as an intermediate for the preparation of protected myo-inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo-inositol derivatives which are intermediates for the preparation of myo-inositol phosphates and racemic ononitol. (C) 1998 Elsevier Science Ltd. All rights reserved.