Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-2,4-bis-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5,6-dihydroxy-cyclohexyl ester | 291527-78-1

• 英文名称: Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-2,4-bis-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5,6-dihydroxy-cyclohexyl ester
• 英文别名: dibenzyl [(1R,2R,3S,4S,5R,6S)-3-bis(phenylmethoxy)phosphoryloxy-4,5-dihydroxy-2,6-bis(phenylmethoxy)cyclohexyl] phosphate
• CAS: 291527-78-1
• 化学式: C₄₈H₅₀O₁₂P₂
• 分子量: 880.865
• InChiKey: ZBMFJOZXOMIUMB-AHYRXPHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-2,4-bis-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5,6-dihydroxy-cyclohexyl ester 在 钯 pyridinium hydrobromide perbromide 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 水 、 三乙胺 为溶剂， -20.0~23.0 ℃ 、358.53 kPa 条件下， 反应 6.5h， 生成 Octanoic acid (S)-2-[hydroxy-((1S,2R,3R,4S,5S,6R)-2,4,6-trihydroxy-3,5-bis-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-1-octanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Concise syntheses of l-α-phosphatidyl-d-myo-inositol 3-phosphate (3-PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)

  摘要：

  Highly efficient, asymmetric total syntheses of the title phospholipids as well as short chain and crosslinkable aminoether analogs were achieved in five to seven steps from a readily available myo-inositol derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00465-2
• 作为产物：
  描述：

  (1'R,3aR,4R,4'R,5S,6S,7R,7aS)-1',7',7'-trimethyl-5,7-bis(phenylmethoxy)spiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,2'-bicyclo[2.2.1]heptane]-4,6-diol 在 四氮唑 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 Phosphoric acid dibenzyl ester (1S,2R,3R,4S,5R,6S)-2,4-bis-benzyloxy-3-(bis-benzyloxy-phosphoryloxy)-5,6-dihydroxy-cyclohexyl ester
  参考文献：
  名称：

  Concise syntheses of l-α-phosphatidyl-d-myo-inositol 3-phosphate (3-PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)

  摘要：

  Highly efficient, asymmetric total syntheses of the title phospholipids as well as short chain and crosslinkable aminoether analogs were achieved in five to seven steps from a readily available myo-inositol derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00465-2