1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol | 147127-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol
• 英文别名: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris[bis(2-cyanoethoxy)phospho]-chiro-inositol；[(1S,2S,3S,4R,5S,6S)-2,4-bis[bis(2-cyanoethoxy)phosphoryloxy]-3,5,6-tris(phenylmethoxy)cyclohexyl] bis(2-cyanoethyl) phosphate
• CAS: 147127-66-0
• 化学式: C₄₅H₅₁N₆O₁₅P₃
• 分子量: 1008.85
• InChiKey: SEHISYHZVPFMMM-CPPKSIGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  69
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  305
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol 在 氨 、 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.08h， 生成 1L-(-)-chiro-inositol 1,4,6-trisphosphoate sodium salt
  参考文献：
  名称：

  Synthesis of Selective Non-Ca2+ Mobilizing Inhibitors of D-myo-Inositol 1,4,5-Trisphosphate 5-Phosphatase

  摘要：

  Syntheses of novel phosphorothioate-based non-Ca2+-releasing inhibitors of myo-inositol 1,4,5-trisphosphate 5-phosphatase are described. 1L-myo-Inositol 1,4,5-trisphosphorothioate, myoinositol 1,3,5-trisphosphorothioate, and 1L-chiro-inositol 1,4,6-trisphosphorothioate have been synthesized from 1L-2,3,6-tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol, 2,4,6-tris-O-(p-methoxybenzyl)-myo-inositol orthoformate and 1L-2,3,5-tri-O-benzyl-chiro-inositol, respectively. 1L-2,3,5-Tri-O-benzyl-chiro-inositol was also used to prepare 1L-chiro-inositol 1,4,6-trisphosphate. The phosphorothioates did not mobilize intracellular Ca2+ but were highly potent inhibitors of Ins(1,4,5)P(3)5-phosphatase, and myo-inositol 1,3,5-trisphosphorothioate and 1L-chiro-inositol 1,4,6-trisphosphorothioate were selective for this enzyme.

  DOI：

  10.1021/jm00033a007
• 作为产物：
  描述：

  双(2-氰乙基)-N,N-二异丙基亚磷酰胺 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol
  参考文献：
  名称：

  Synthesis of Selective Non-Ca2+ Mobilizing Inhibitors of D-myo-Inositol 1,4,5-Trisphosphate 5-Phosphatase

  摘要：

  Syntheses of novel phosphorothioate-based non-Ca2+-releasing inhibitors of myo-inositol 1,4,5-trisphosphate 5-phosphatase are described. 1L-myo-Inositol 1,4,5-trisphosphorothioate, myoinositol 1,3,5-trisphosphorothioate, and 1L-chiro-inositol 1,4,6-trisphosphorothioate have been synthesized from 1L-2,3,6-tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol, 2,4,6-tris-O-(p-methoxybenzyl)-myo-inositol orthoformate and 1L-2,3,5-tri-O-benzyl-chiro-inositol, respectively. 1L-2,3,5-Tri-O-benzyl-chiro-inositol was also used to prepare 1L-chiro-inositol 1,4,6-trisphosphate. The phosphorothioates did not mobilize intracellular Ca2+ but were highly potent inhibitors of Ins(1,4,5)P(3)5-phosphatase, and myo-inositol 1,3,5-trisphosphorothioate and 1L-chiro-inositol 1,4,6-trisphosphorothioate were selective for this enzyme.

  DOI：

  10.1021/jm00033a007