Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5S,6R)-2,3,4-tris-(bis-benzyloxy-phosphoryloxy)-5,6-difluoro-cyclohexyl ester | 214154-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5S,6R)-2,3,4-tris-(bis-benzyloxy-phosphoryloxy)-5,6-difluoro-cyclohexyl ester
• CAS: 214154-10-6
• 化学式: C₆₂H₆₂F₂O₁₆P₄
• 分子量: 1225.06
• InChiKey: FYVGEDOLQNSYNQ-KKWMHNGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.38
• 重原子数：
  84.0
• 可旋转键数：
  32.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5S,6R)-2,3,4-tris-(bis-benzyloxy-phosphoryloxy)-5,6-difluoro-cyclohexyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 octasodium D-2,3-dideoxy-2,3-difluoro-myo-inositol 1,4,5,6-tetrakisphosphate
  参考文献：
  名称：

  Synthesis of d-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

  摘要：

  DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of 0-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00146-3
• 作为产物：
  描述：

  D-1,4,5,6-tetra-O-benzyl-2,3-dideoxy-2,3-difluoro-myo-inositol 在 palladium on activated charcoal 四氮唑 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5S,6R)-2,3,4-tris-(bis-benzyloxy-phosphoryloxy)-5,6-difluoro-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of d-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer as analogues of myo-inositol 3,4,5,6-tetrakisphosphate

  摘要：

  DL-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-scyllo-inositol was resolved using (-)-(1S, 4R)-camphanyl chloride. The diastereoisomers formed were separated and the structure of D-3,4,5,6-tetra-O-benzyl-2-(1S,4R)-camphanyl-1-deoxy-1-fluoro-scyllo-inositol was solved by X-ray crystallography to an R-factor of 4.2%. A series of manipulations led to the preparation of 0-1,2-dideoxy-1,2-difluoro-myo-inositol 3,4,5,6-tetrakisphosphate and its enantiomer. The D-1,2-difluoro enantiomer stereospecifically inhibited CaMK II-activated Cl- current, but with low potency; however, efficacy of this compound was greatly enhanced by myo-inositol 3,4,5,6-tetrakisphosphate itself. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00146-3