(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 | 864372-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (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
• 英文别名: dibenzyl [(1S,4S,5R,6R)-4-bis(phenylmethoxy)phosphoryloxy-5,6-bis[(3-oxo-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepin-3-yl)oxy]cyclohex-2-en-1-yl] phosphate；dibenzyl [(1S,4S,5R,6R)-4-bis(phenylmethoxy)phosphoryloxy-5,6-bis[(3-oxo-1,5-dihydro-2,4,3λ5-benzodioxaphosphepin-3-yl)oxy]cyclohex-2-en-1-yl] phosphate
• CAS: 864372-82-7
• 化学式: C₅₀H₅₀O₁₆P₄
• 分子量: 1030.83
• InChiKey: WAXFBTZMOODYAC-NDQIPAMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  70
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 在 吡啶 、 四氮唑 、 氢氧化钾 、 sodium tetrahydroborate 、 4 A molecular sieve 、 phosphate buffer pH=7 、 pig pancreas lipase 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 127.5h， 生成 (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
  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