1,3,4-tri-O-benzoyl-D-myo-inositol | 136845-94-8

• 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: 1,3,4-tri-O-benzoyl-D-myo-inositol
• 英文别名: D-1,3,4-tri-O-benzoyl-myo-inositol；[(1S,2S,3S,4S,5R,6R)-3,4-dibenzoyloxy-2,5,6-trihydroxycyclohexyl] benzoate
• CAS: 136845-94-8
• 化学式: C₂₇H₂₄O₉
• 分子量: 492.482
• InChiKey: VCMNAXSEEQVJPM-PPOWDTIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-benzoyl-D-myo-inositol 在 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 12.0h， 生成 (1R,2R,3R,4R,5S,6S)-3,5,6-tris(phosphonooxy)cyclohexane-1,2,4-triyl tribenzoate
  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-1,2,6-tri-O-benzoyl-myo-inositol 在 吡啶 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1,3,4-tri-O-benzoyl-D-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

• Synthesis and Ca2+-release activity of d- and l-myo-inositol 2,4,5-trisphosphate and d- and l-chiro-inositol 1,3,4-trisphosphate
  作者：Werner Tegge、Gerald V. Denis、Clinton E. Ballou

  DOI：10.1016/0008-6215(91)84121-t

  日期：1991.9

  Partial benzoylation of the 3,4-dibenzyl ethers of D- and L-chiro-inositol provided the 1,2,5-tri-O-benzoyl-3,4-di-O-benzyl-chiro-inositols. Inversion of the free axial hydroxyl group gave a mixture of chiral 1,3,4- and 1,2,4-tri-O-benzoyl-5,6-di-O-benzyl-myo-inositols [W. Tegge and C. E. Ballou, Proc. Natl. Acad. Sci. U.S.A., 86 (1989) 94-98]. Catalytic hydrogenolysis cleaved the benzyl ether groups

  D-和L-手性肌醇的3，4-二苄基醚的部分苯甲酰化提供了1,2,5-三-O-苯甲酰基-3,4-二-O-苄基-手性肌醇。游离轴向羟基的转化得到手性1,3,4-和1,2,4-三-O-苯甲酰基-5,6-二-O-苄基-肌醇的混合物[W. Tegge和CE Ballou，公司 Natl。学院 科学 美国，86（1989）94-98]。催化氢解裂解1,3,4-三-O-苯甲酰基-5,6-二-O-苄基-肌醇（D-和L-）的苄基醚，得到1,3,4-通过二苄基亚磷酰胺方法将其磷酸化的三-O-苯甲酰基-肌醇。除去所有封闭基团，得到纯的对映体的肌醇2,4,5-三磷酸酯。手性肌醇1,3,4-三磷酸酯的合成物，类似于在位置1具有轴向磷酸酯基的肌醇1,4,5-三磷酸酯的类似物。或从位置1、1,2,5-三-O-苯甲酰基-3,4-二-O-苄基-开始设计的具有1位轴向羟基的肌醇2,4,5-三磷酸的类似物手性肌醇。在用皂素通透