methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside | 637774-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-6-methoxy-2-(4-methoxyphenyl)-7,8-di(tetradecoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 637774-18-6
• 化学式: C₄₃H₇₆O₇
• 分子量: 705.072
• InChiKey: UPHHCUZDEONZAE-ZKABDHPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  50
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime
  参考文献：
  名称：

  Synthesis and biological evaluation of novel lipid A antagonists

  摘要：

  A mimetic of Lipid A with a beta-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its beta-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Escherichia coli lipid A on MT2 macrophages in a dose-dependent manner, while they were completely devoid of inflammatory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.047
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 methyl 4,6-O-(4-methoxybenzylidene)-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of novel lipid A antagonists

  摘要：

  A mimetic of Lipid A with a beta-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its beta-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Escherichia coli lipid A on MT2 macrophages in a dose-dependent manner, while they were completely devoid of inflammatory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.047

文献信息

• Saccharide conjugates
  申请人：Demchenko Alexei

  公开号：US09120838B2

  公开（公告）日：2015-09-01

  The invention provides a series of novel Lipid A analogs that are structually simple, synthetically accessible, and capable of blocking the cellular receptor within the signal transduction pathway. The novel Lipid A analogs can include a monosaccharide core with hydrophobic side chains and amino acid ionic motif. The invention further provides methods of using the compounds and compositions thereof in various therapeutic methods.

  这项发明提供了一系列新颖的脂多糖A类似物，这些类似物在结构上简单，易于合成，并能够阻断信号转导途径内的细胞受体。这些新颖的脂多糖A类似物可以包括一个单糖核心，带有疏水侧链和氨基酸离子基序。该发明还提供了在各种治疗方法中使用这些化合物及其组合物的方法。
• LIPID A ANTAGONISTS WITH ANTI-SEPTIC SHOCK, ANTI-INFLAMMATORY, ANTI-ISCHEMIA AND ANALGESIC ACTIVITY
  申请人：Università Degli Studi Di Milano - Bicocca

  公开号：EP1996603B1

  公开（公告）日：2009-07-15