(2-O-arachidyl-1-O-stearyl-sn-glycer-3-yl)(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)phosphate triethylammonium salt | 1065484-03-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (2-O-arachidyl-1-O-stearyl-sn-glycer-3-yl)(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)phosphate triethylammonium salt
• CAS: 1065484-03-8
• 化学式: C₆H₁₅N*C₇₅H₁₁₅O₁₃P
• 分子量: 1356.9
• InChiKey: JPRBVDRYTTVUME-PFSODISTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.92
• 重原子数：
  96.0
• 可旋转键数：
  58.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  157.75
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2-O-arachidyl-1-O-stearyl-sn-glycer-3-yl)(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)phosphate triethylammonium salt 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以97%的产率得到(2-O-arachidyl-1-O-stearyl-sn-glycer-3-yl) β-D-mannopyranosyl phosphate triethylammonium salt
  参考文献：
  名称：

  Syntheses of phosphatidyl-β-d-glucoside analogues to probe antigen selectivity of monoclonal antibody ‘DIM21’

  摘要：

  Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.041
• 作为产物：
  描述：

  2-O-arachidyl-1-O-stearyl-sn-glycerol 、 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl hydrogenphosphate triethylammonium salt 在 吡啶 、 三甲基乙酰氯 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 以43%的产率得到(2-O-arachidyl-1-O-stearyl-sn-glycer-3-yl)(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)phosphate triethylammonium salt
  参考文献：
  名称：

  Syntheses of phosphatidyl-β-d-glucoside analogues to probe antigen selectivity of monoclonal antibody ‘DIM21’

  摘要：

  Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.041