(2R)-3-(benzyloxy(diisopropylamino)phosphinooxy)-2-(stearoyloxy)propyl phenyl succinate | 1514617-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (2R)-3-(benzyloxy(diisopropylamino)phosphinooxy)-2-(stearoyloxy)propyl phenyl succinate
• CAS: 1514617-86-7
• 化学式: C₄₄H₇₀NO₈P
• 分子量: 772.015
• InChiKey: NIHPXZOONCIYPT-CTEKKXEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.67
• 重原子数：
  54.0
• 可旋转键数：
  32.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  100.6
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R)-3-(benzyloxy(diisopropylamino)phosphinooxy)-2-(stearoyloxy)propyl phenyl succinate 、 3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol 在 四氮唑 、 双氧水 作用下， 以 二氯甲烷 、 乙腈 、 水 为溶剂， 反应 2.5h， 以30%的产率得到(2R)-3-(benzyloxy((1S,2R,3S,4S,5R,6R)-2,4,6-tris(benzyloxy)-3-((bis(benzyloxy)phosphoryl)methyl)-5-hydroxycyclohexyloxy)phosphoryloxy)-2-(stearoyloxy)propyl phenyl succinate
  参考文献：
  名称：

  A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation

  摘要：

  We report the synthesis and biochemical validation of a phosphatidyl inositol-3 phosphate (PI3P) immunogen. The inositol stereochemistry was secured through peptide-catalyzed asymmetric phosphorylation catalysis, and the subsequent incorporation of a cysteine residue was achieved by native chemical ligation (NCL). Conjugation of the PI3P hapten to maleimide-activated keyhole limpet hemocyanin (KLH) provided a PI3P immunogen, which was successfully used to generate selective PI3P antibodies. The incorporation of a sulfhydryl nucleophile into a phosphoinositide hapten demonstrates a general strategy to reliably access phosphoinositide immunogens.

  DOI：

  10.1021/ja410750a
• 作为产物：
  描述：

  (S)-2-hydroxy-3-(4-methoxybenzyloxy)propyl phenyl succinate 在 四氮唑 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.08h， 生成 (2R)-3-(benzyloxy(diisopropylamino)phosphinooxy)-2-(stearoyloxy)propyl phenyl succinate
  参考文献：
  名称：

  A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation

  摘要：

  We report the synthesis and biochemical validation of a phosphatidyl inositol-3 phosphate (PI3P) immunogen. The inositol stereochemistry was secured through peptide-catalyzed asymmetric phosphorylation catalysis, and the subsequent incorporation of a cysteine residue was achieved by native chemical ligation (NCL). Conjugation of the PI3P hapten to maleimide-activated keyhole limpet hemocyanin (KLH) provided a PI3P immunogen, which was successfully used to generate selective PI3P antibodies. The incorporation of a sulfhydryl nucleophile into a phosphoinositide hapten demonstrates a general strategy to reliably access phosphoinositide immunogens.

  DOI：

  10.1021/ja410750a