Butyric acid (S)-1-butyryloxymethyl-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: Butyric acid (S)-1-butyryloxymethyl-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester
• 英文别名: D-Myo-phosphatidylinositol 3-phosphated (+)-SN-1,2-DI-O-butanoylglyceryl,3-O-phospho；[(2S)-2-butanoyloxy-3-[hydroxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxycyclohexyl]oxyphosphoryl]oxypropyl] butanoate
• 化学式: C₁₇H₃₂O₁₆P₂
• 分子量: 554.379
• InChiKey: NKJZZWLREOAJGO-HODIZBBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  Butyric acid (S)-2-{benzyloxy-[(1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyloxy]-phosphoryloxy}-1-butyryloxymethyl-ethyl ester 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 水 、 叔丁醇 为溶剂， 反应 5.0h， 以92%的产率得到Butyric acid (S)-1-butyryloxymethyl-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonooxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

  摘要：

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.

  DOI：

  10.1021/jo980501r