D-2,3-O-cyclohexylidene-1-O-(dibenzylphosphoryl)-4,5-di-O-(o-xylylenephosphoryl)-myo-inositol | 627084-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-2,3-O-cyclohexylidene-1-O-(dibenzylphosphoryl)-4,5-di-O-(o-xylylenephosphoryl)-myo-inositol
• 英文别名: [(3aR,4S,5S,6R,7R,7aS)-5-hydroxy-6,7-bis[(3-oxo-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepin-3-yl)oxy]spiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl] dibenzyl phosphate；[(3aR,4S,5S,6R,7R,7aS)-5-hydroxy-6,7-bis[(3-oxo-1,5-dihydro-2,4,3λ5-benzodioxaphosphepin-3-yl)oxy]spiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl] dibenzyl phosphate
• CAS: 627084-29-1
• 化学式: C₄₂H₄₇O₁₅P₃
• 分子量: 884.747
• InChiKey: NSHNYWMKPZFJIP-BDPXDZDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  60
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  D-2,3-O-cyclohexylidene-1-O-(dibenzylphosphoryl)-4,5-di-O-(o-xylylenephosphoryl)-myo-inositol 在 palladium on activated charcoal 三正丁胺 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以100%的产率得到Trisodium (1R,2R,3S,4R,5R,6S)-3,5,6-trihydroxy-1,2,4-cyclohexanet riyl tris[hydrogen (phosphate)]
  参考文献：
  名称：

  Regioselective phosphorylation of vicinal 3,4-hydroxy myo-inositol derivative promoted practical synthesis of d-PtdIns(4,5)P2 and d-Ins(1,4,5)P3

  摘要：

  The reactivity of 3 and 4-OH in 3,4-diol myo-inositol derivatives were observed through the phosphorylation, acylation and silylation. The results indicated that 3-OH is much more reactive than 4-OH, giving regiospecifically 3-mono-functionalized products. This investigation provided a concise methodology for the synthesis of natural D-form of PtdIns(4,5)P2 and D-Ins(1,4,5)P3 from L-1,2-O-cyclohexylidene-3,4-O-(tetraisopropyl disiloxane-1,3-diyl)-myo-inositol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01212-2
• 作为产物：
  描述：

  L-1,2-O-cyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol 在 2,6-二甲基吡啶 、 四氮唑 、 四丁基氟化铵 、 溶剂黄146 、 pyridinium hydrobromide perbromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 D-2,3-O-cyclohexylidene-1-O-(dibenzylphosphoryl)-4,5-di-O-(o-xylylenephosphoryl)-myo-inositol
  参考文献：
  名称：

  Regioselective phosphorylation of vicinal 3,4-hydroxy myo-inositol derivative promoted practical synthesis of d-PtdIns(4,5)P2 and d-Ins(1,4,5)P3

  摘要：

  The reactivity of 3 and 4-OH in 3,4-diol myo-inositol derivatives were observed through the phosphorylation, acylation and silylation. The results indicated that 3-OH is much more reactive than 4-OH, giving regiospecifically 3-mono-functionalized products. This investigation provided a concise methodology for the synthesis of natural D-form of PtdIns(4,5)P2 and D-Ins(1,4,5)P3 from L-1,2-O-cyclohexylidene-3,4-O-(tetraisopropyl disiloxane-1,3-diyl)-myo-inositol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01212-2