Phosphoric acid benzyl ester (S)-3-{benzyloxy-[(R)-3-{benzyloxy-[(R)-3-hydroxy-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propyl ester (S)-2,3-bis-benzyloxy-propyl ester | 849357-05-7

• 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: Phosphoric acid benzyl ester (S)-3-{benzyloxy-[(R)-3-{benzyloxy-[(R)-3-hydroxy-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propyl ester (S)-2,3-bis-benzyloxy-propyl ester
• CAS: 849357-05-7
• 化学式: C₇₁H₈₃O₂₁P₃
• 分子量: 1365.35
• InChiKey: BIZOWNSBXBVKKY-FNUJXZQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.64
• 重原子数：
  95.0
• 可旋转键数：
  47.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  228.35
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  Diisopropyl-phosphoramidous acid benzyl ester (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl ester 、 Phosphoric acid benzyl ester (S)-3-{benzyloxy-[(R)-3-{benzyloxy-[(R)-3-hydroxy-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propyl ester (S)-2,3-bis-benzyloxy-propyl ester 在 四氮唑 作用下， 生成
  参考文献：
  名称：

  合成第一个完全活性的脂磷壁酸。

  摘要：

  DOI：

  10.1002/anie.200390243
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到Phosphoric acid benzyl ester (S)-3-{benzyloxy-[(R)-3-{benzyloxy-[(R)-3-hydroxy-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propoxy]-phosphoryloxy}-2-(4-methoxy-benzyloxy)-propyl ester (S)-2,3-bis-benzyloxy-propyl ester
  参考文献：
  名称：

  Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA)

  摘要：

  Based on 1,2-O-isopropylidene-sn-glyerol, which is readily available from D-mannitol, five chiral building blocks for the construction of structural variants of Staphylococcus aureus LTA designed and synthesized. Ligation of these building blocks led readily to the target molecules 1 and 2. They demonstrated that the D-alanine residues at the glycerophosphate backbone are decisive for the activation of the immune system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.070

文献信息

• Synthesis of Staphylococcus aureus lipoteichoic acid derivatives for determining the minimal structural requirements for cytokine induction
  作者：Ignacio Figueroa-Perez、Andreas Stadelmaier、Susanne Deininger、Sonja von Aulock、Thomas Hartung、Richard R. Schmidt

  DOI：10.1016/j.carres.2006.10.003

  日期：2006.12

  For the investigation of the minimal structural requirements for cytokine induction, Staphylococcus aureus lipoteichoic acid derivatives with two, three, four, and five glycerophosphate backbone moieties, carrying each a D-alanyl residue, were needed. Based on two different glycerophosphate building blocks and 6b-O-phosphitylated gentiobiosyl diacylglycerol the desired target molecules (compounds 1-4) could be readily obtained and provided for biological studies. (c) 2006 Elsevier Ltd. All rights reserved.