2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl hydrogenphosphate triethylammonium salt | 1065483-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl hydrogenphosphate triethylammonium salt
• CAS: 1065483-75-1
• 化学式: C₆H₁₅N*C₃₄H₃₇O₈P
• 分子量: 705.829
• InChiKey: BVZIRCHWHHPKPB-KLURGWPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  50.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 、 三乙胺 在 亚磷酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以52%的产率得到2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl hydrogenphosphate 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

文献信息

• Hydrogenphosphonate synthesis of sugar phosphomonoesters
  作者：Dmitry V. Yashunsky、Andrei V. Nikolaev

  DOI：10.1039/b000727g

  日期：——

  A highly efficient procedure for the phosphorylation of sugar hydroxy derivatives has been developed. A four-step sequence comprising H-phosphonate formation, pivaloyl chloride-mediated coupling with fluoren-9-ylmethanol, oxidation, and cleavage of the fluoren-9-ylmethyl ester led to the sugar monophosphate derivatives 4a–g in 83–93% yield.

  已经开发了一种高效的糖羟基衍生物磷酸化程序。该程序包括四个步骤：H-磷酸酯的形成、与弗罗伦-9-甲醇的pivaloyl氯介导的耦合、氧化以及弗罗伦-9-甲基酯的裂解，最终获得糖单磷酸衍生物4a-g，产率为83-93%。