Diisopropyl-phosphoramidous acid benzyl ester (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl ester | 544686-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Diisopropyl-phosphoramidous acid benzyl ester (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl ester
• CAS: 544686-86-4
• 化学式: C₄₀H₅₄NO₅PSi
• 分子量: 687.932
• InChiKey: JEZDGKRCSOIZQJ-WFXJVPPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.74
• 重原子数：
  48.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.39
• 氢给体数：
  0.0
• 氢受体数：
  6.0

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 在 四氮唑 、 叔丁基过氧化氢 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzyl [(2S)-1,2-di-benzyloxy-propan-3-yl] [(2R)-1-hydroxy-2-(4-methoxybenzyloxy)propan-3-yl] phosphate
  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
• 作为产物：
  描述：

  tert-Butyl-{(S)-2-(4-methoxy-benzyloxy)-3-[((E)-propenyl)oxy]-propoxy}-diphenyl-silane 在 四氮唑 、 盐酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.67h， 生成 Diisopropyl-phosphoramidous acid benzyl ester (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-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 the First Fully Active Lipoteichoic Acid
  作者：Andreas Stadelmaier、Siegfried Morath、Thomas Hartung、Richard R. Schmidt

  DOI：10.1002/anie.200390243

  日期：2003.2.24
• A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues
  作者：A STADELMAIER、I FIGUEROAPEREZ、S DEININGER、S VONAULOCK、T HARTUNG、R SCHMIDT

  DOI：10.1016/j.bmc.2006.05.055

  日期：2006.9.15

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.