L-1,4-di-O-benzoyl-myo-inositol | 253683-74-8

• 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-1,4-di-O-benzoyl-myo-inositol
• CAS: 253683-74-8
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: HHFURBLRRVMWNI-SJUNHDGSSA-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：

  L-1,4-di-O-benzoyl-myo-inositol 在 10percent Pd/C 四氮唑 、 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 31.0h， 生成 DL-3,6-di-O-benzoyl-myo-inositol 1,2,4,5-tetrakisphosphate
  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：

  [(1S,2S,3R,4S,5R,6R)-4-benzoyloxy-2,3-dihydroxy-5,6-bis(2,2,2-trichloroethoxycarbonyloxy)cyclohexyl] benzoate 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到L-1,4-di-O-benzoyl-myo-inositol
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Transformations of Conduritol B Tetracarboxylates:  An Asymmetric Synthesis of d-myo-Inositol 1,4,5-Trisphosphate

  摘要：

  DOI：

  10.1021/ja992960v