L-1,6-di-O-benzoyl-myo-inositol | 165883-87-4

• 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: L-1,6-di-O-benzoyl-myo-inositol
• 英文别名: [(1S,2S,3R,4S,5S,6S)-2-benzoyloxy-3,4,5,6-tetrahydroxycyclohexyl] benzoate
• CAS: 165883-87-4
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: FRVGAZBPNHEBBF-WJWMFLMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-1,6-di-O-benzoyl-myo-inositol 在 吡啶 、 lithium hydroxide 、 三甲基溴硅烷 、 sodium phosphate buffer 、 水 、 双氧水 、 溶剂黄146 、 N,N-二异丙基乙胺 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 20.0h， 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-3,4-O-isopropylidene-myo-inositol 在 吡啶 、 水 、 溶剂黄146 作用下， 生成 L-1,6-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

• 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。
• Receptor Specific Binder Discovery Using Intramolecular Acyl Migration Induced Dynamic Carbohydrate Library
  申请人：Chang Young-Tae

  公开号：US20080119373A1

  公开（公告）日：2008-05-22

  An efficient molecular evolution system was obtained by combining two novel approaches in the field, intramolecular acyl migration for DCL generation and boronic acid as a selector. 1,4-Di-O-benzoyl chiro-inositol in acetonitrile with DBU as a base generated a reversible equilibrium of 9 regioisomers. Only 3,4-di-O-benzoyl chiro-inositol, containing two sets of cis-diols, is most favored toward binding with phenyl boronic acid, and its percentage of the DCL composition was amplified by up to 82%.
• [EN] RECEPTOR SPECIFIC BINDER DISCOVERY USING INTRAMOLECULAR ACYL MIGRATION INDUCED DYNAMIC CARBOHYDRATE LIBRARY<br/>[FR] DECOUVERTE DE LIANT SPECIFIQUE DE RECEPTEUR AU MOYEN D'UNE BIBLIOTHEQUE DE CARBOHYDRATE DYNAMIQUE INDUITE PAR MIGRATION ACYLE INTRAMOLECULAIRE
  申请人：UNIV NEW YORK

  公开号：WO2005033149A1

  公开（公告）日：2005-04-14

  An efficient molecular evolution system was obtained by combining two novel approaches in the field, intramolecular acyl migration for DCL generation and boronic acid as a selector. 1,4-Di-O-benzoyl chiro-inositol in acetonitrile with DBU as a base generated a reversible equilibrium of 9 regioisomers. Only 3,4-di-O-benzoyl chiro-inositol, containing two sets of cis-diols, is most favored toward binding with phenyl boronic acid, and its percentage of the DCL composition was amplified by up to 82%.