methyl 2,3-di-O-methyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside | 1619942-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-methyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside
• CAS: 1619942-52-7
• 化学式: C₂₀H₃₆O₁₀
• 分子量: 436.5
• InChiKey: PUNKHQGPHQETTD-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  30.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  、 methyl 2,3-di-O-methyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside 在 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以50%的产率得到
  参考文献：
  名称：

  Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies

  摘要：

  In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor anti-bacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.018
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 26.75h， 生成 methyl 2,3-di-O-methyl-6-O-(2,5,8,11,14-pentaoxaheptadec-16-ynyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies

  摘要：

  In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor anti-bacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.018