L-1,2-O-cyclohexylidene-5,6-di-O-(o-xylylenephosphoryl)-myo-inositol | 524047-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-1,2-O-cyclohexylidene-5,6-di-O-(o-xylylenephosphoryl)-myo-inositol
• 英文别名: (3aS,4S,5S,6R,7R,7aS)-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]-4,5-diol；(3aS,4S,5S,6R,7R,7aS)-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]-4,5-diol
• CAS: 524047-36-7
• 化学式: C₂₈H₃₄O₁₂P₂
• 分子量: 624.518
• InChiKey: YVURIHNIRRUWIV-QZQCWTALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  L-1,2-O-cyclohexylidene-5,6-di-O-(o-xylylenephosphoryl)-myo-inositol 在 palladium on activated charcoal 2,6-二甲基吡啶 、 三正丁胺 、 氢气 、 pyridinium hydrobromide perbromide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 74.17h， 生成 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：

  3-(二乙氨基)-1,5-二氢-2,4,3-苯并二噁磷杂庚英 在 四氮唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.08h， 生成 L-1,2-O-cyclohexylidene-5,6-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

文献信息

• A Short Synthesis of Dipalmitoylphosphatidylinositol 4,5-Bisphosphate via 3-<i>O</i>-Selective Phosphorylation of a 3,4-Free Inositol Derivative
  作者：Fushe Han、Minoru Hayashi、Yutaka Watanabe

  DOI：10.1246/cl.2003.46

  日期：2003.1

  Dipalmitoylphosphatidylinositol 4,5-bisphosphate was conveniently synthesized via the regioselective phosphorylation of l-1,2-O-cyclohexylidene-5,6-di-O-(o-xylylene phosphoryl)-myo-inositol derived from 1,2-O-cyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol.

  通过l-1,2-O-环己亚基-5,6-二-O-(邻苯二甲酰亚胺基磷酰)-肌醇（源自1,2-O-环己亚基-3,4-O-(四异丙基二硅氧烷-1,3-二基)-肌醇）的位点选择性磷酸化，可以方便地合成二棕榈酰磷脂酰肌醇 4,5-二磷酸酯。