1,2-O-isopropylidene-3-O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl]-sn-glycerol | 544687-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-O-isopropylidene-3-O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl]-sn-glycerol
• CAS: 544687-08-3
• 化学式: C₆₇H₆₀O₂₀
• 分子量: 1185.2
• InChiKey: LSZGEXIUANAYSM-NLPVNNOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  87.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  239.48
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl]-sn-glycerol 在 吡啶 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 1,2-O-isopropylidene-3-O-[6-O-(6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-sn-glycerol
  参考文献：
  名称：

  A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.05.055
• 作为产物：
  描述：

  6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-D-glucopyranose 在 3 A molecular sieve 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 1,2-O-isopropylidene-3-O-[6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl]-sn-glycerol
  参考文献：
  名称：

  A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.05.055

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