methyl 6-methoxyamino-2,3-di-O-tetradecyl-6-deoxy-6-N-(4,6-di-O-acetyl-2,3-di-O-tetradecyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 872677-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-methoxyamino-2,3-di-O-tetradecyl-6-deoxy-6-N-(4,6-di-O-acetyl-2,3-di-O-tetradecyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS: 872677-71-9
• 化学式: C₇₄H₁₄₃NO₁₃
• 分子量: 1254.95
• InChiKey: SMNDZRDLRLGHBI-VRHGTFBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.15
• 重原子数：
  88.0
• 可旋转键数：
  64.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  149.91
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl 6-methoxyamino-2,3-di-O-tetradecyl-6-deoxy-6-N-(4,6-di-O-acetyl-2,3-di-O-tetradecyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以100%的产率得到methyl 2,3-di-O-tetradecyl-6-deoxy-6-methoxyamino-6-N-(2,3-di-O-tetradecyl-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：

  methyl 4-O-(4-methoxybenzyl)-2,3-di-O-tetradecyl-α-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 溶剂黄146 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 methyl 6-methoxyamino-2,3-di-O-tetradecyl-6-deoxy-6-N-(4,6-di-O-acetyl-2,3-di-O-tetradecyl-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