Acetic acid (2R,3R,4S,5R)-2-acetoxymethyl-4,5-bis-tetradecyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester | 872677-72-0

• 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: Acetic acid (2R,3R,4S,5R)-2-acetoxymethyl-4,5-bis-tetradecyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• CAS: 872677-72-0
• 化学式: C₄₀H₇₂Cl₃NO₈
• 分子量: 801.373
• InChiKey: UZNBALLXHQSOTP-OXODQGHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.74
• 重原子数：
  52.0
• 可旋转键数：
  32.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  113.37
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-glucopyranoside 、 Acetic acid (2R,3R,4S,5R)-2-acetoxymethyl-4,5-bis-tetradecyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2,3-di-O-tetradecyl-4-O-p-methoxybenzyl-6-O-(2,3-di-O-tetradecyl-4,6-di-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 、 methyl 2,3-di-O-tetradecyl-4-O-p-methoxybenzyl-6-O-(2,3-di-O-tetradecyl-4,6-di-O-acetyl-β-D-glucopyranosyl)-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
• 作为产物：
  描述：

  1,4,6-tri-O-acetyl-2,3-di-O-tetradecyl-D-glucopyranoside 在 乙酸肼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 Acetic acid (2R,3R,4S,5R)-2-acetoxymethyl-4,5-bis-tetradecyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  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