D-myo-3,6-bis-O-(di-O-benzylphospho)-4,5-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)inositol | 222420-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-myo-3,6-bis-O-(di-O-benzylphospho)-4,5-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)inositol
• 英文别名: dibenzyl [(1S,2R,3S,4S,5R,6R)-4-bis(phenylmethoxy)phosphoryloxy-2,3-dihydroxy-5,6-bis[(3-oxo-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepin-3-yl)oxy]cyclohexyl] phosphate；dibenzyl [(1S,2R,3S,4S,5R,6R)-4-bis(phenylmethoxy)phosphoryloxy-2,3-dihydroxy-5,6-bis[(3-oxo-1,5-dihydro-2,4,3λ5-benzodioxaphosphepin-3-yl)oxy]cyclohexyl] phosphate
• CAS: 222420-83-9
• 化学式: C₅₀H₅₂O₁₈P₄
• 分子量: 1064.85
• InChiKey: JGCRRDVBDLPVJS-KSJHZKFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  72
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  D-myo-3,6-bis-O-(di-O-benzylphospho)-4,5-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)inositol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到[(1R,2S,3S,4R,5S,6R)-3,4-二羟基-2,5,6-三膦酰氧基环己基]磷酸二氢酯
  参考文献：
  名称：

  Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

  摘要：

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.

  DOI：

  10.1021/jm981113k
• 作为产物：
  描述：

  (1S,2S,3S,4S)-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)conduritol-B 在 ruthenium trichloride 、 sodium periodate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 0.17h， 以86%的产率得到D-myo-3,6-bis-O-(di-O-benzylphospho)-4,5-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)inositol
  参考文献：
  名称：

  Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

  摘要：

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.

  DOI：

  10.1021/jm981113k