3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol | 454198-20-0

• 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: 3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol
• 英文别名: D-1,6-di-O-benzoyl-2,3:4,5-di-O-isopropylidene-myo-inositol；[(1R,2R,6S,7R,8R,9R)-8-benzoyloxy-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl] benzoate
• CAS: 454198-20-0
• 化学式: C₂₆H₂₈O₈
• 分子量: 468.504
• InChiKey: LKUQYXYEYUYVGD-BPIQYHPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 在 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 25.0h， 生成 D-1,2,6-tri-O-benzoyl-3,4-O-isopropylidene-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
• 作为产物：
  描述：

  苯甲酰氯 、 23:45-二异亚丙基-肌醇 在 吡啶 作用下， 反应 6.0h， 以96%的产率得到3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-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

• Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate
  作者：Adiyala Vidyasagar、Atchutarao Pathigoolla、Kana M. Sureshan

  DOI：10.1039/c3ob40789f

  日期：——

  cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection–deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization

  天然磷酸肌醇参与各种细胞信号转导过程，以及合成肌醇衍生物在催化，超分子化学，天然产物合成等方面的应用，推动了动力的发展。肌肌醇化学。六个仲羟基的存在需要合成肌醇衍生物的有效保护-去保护策略。初步保护艾滋病的重要策略肌肌醇是二缩酮化，它给出了三个二缩酮的混合物，每个二缩酮同时具有顺式和反式稠合的缩酮。重要的是具有方法学以选择性地水解两个缩酮之一或将两个酸不稳定缩酮之一转化为正交的碱不稳定保护基。通过利用反式-缩酮和顺式-缩酮之间的应变差异，我们开发了两种操作简单，高产的方法，用于肌醇的反式-缩酮（异丙基和环己二烯）的化学选择性水解/乙解，而顺式-缩酮不受干扰，使用便宜且易于制备的H 2 SO 4-二氧化硅作为催化剂。同样，碳水化合物和无环多元醇的末端缩酮部分可以被选择性地水解/乙酰水解，而保留内部的缩酮完整。指某东西的用途甲醇 作为溶剂会导致化学选择性醇解，但使用DCM和 醋酸酐导致化学选择性乙酰分解。应用这种方法，短合成d
• Competition between Non-Classical Single and Double Epimerizations in Cyclitol Chemistry
  作者：Ralf Miethchen、Katharina Neitzel、Kathrin Weise、Manfred Michalik、Helmut Reinke、Franziska Faltin

  DOI：10.1002/ejoc.200300688

  日期：2004.5

  reagent system gave cyclic acetals with one epimerized chiral ring atom and also with two epimerized chiral centres. The single epimerization takes place exclusively at the middle C-atom of the cis-trans triol unit in the tetrol sequence (products 15, 17, 19/20 and 24−27), whereas the double epimerization occurs at both of the "centrally located" C-atoms in the cis-trans-trans tetrol unit (products

  在四个 cyclitol 中研究了两个竞争性区域选择性和立体选择性差向异构化反应，其特征在于四个连续的 OH 基团具有顺-反-反序列，以及与该四醇单元相邻的不同取代基（OMe、OBz、F、H）。起始材料由 L-白木糖醇（化合物 5-7）和肌醇（化合物 8）合成。它们与氯醛/DCC 试剂系统的缩醛化得到具有一个差向异构化手性环原子和两个差向异构化手性中心的环状缩醛。单差向异构化仅发生在四醇序列（产物 15、17、19/20 和 24-27）中顺反三醇单元的中间 C 原子上，而双差向异构化发生在两个“中心位置” " 顺-反-反四醇单元中的碳原子（产物 16、18、21 和 28）。单、双反转化合物的产物比例变化如下：与四醇单元相邻的取代基的吸电子效应越低，相应双反转产物的百分比越高。但是，在所有情况下，单倒置产品仍然是主要产品。对原料 1-氟-2-O-(甲基)环己烷-2,3,4,5,6-戊醇 (5)
• US5278332A
  申请人：——

  公开号：US5278332A

  公开（公告）日：1994-01-11
• Divergent Syntheses of All Possible Optically Active Regioisomers of <i>m</i><i>yo</i>-Inositol Tris- and Tetrakisphosphates
  作者：Sung-Kee Chung、Yong-Uk Kwon、Jung-Han Shin、Young-Tae Chang、Changgook Lee、Boo-Gyo Shin、Kyung-Cheol Kim、Mahn-Joo Kim

  DOI：10.1021/jo0257694

  日期：2002.8.1

  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.