(3R,4S,5R,6R)-2,3,4,5-Tetrakis-allyloxy-6-allyloxymethyl-tetrahydro-pyran

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R,6R)-2,3,4,5-Tetrakis-allyloxy-6-allyloxymethyl-tetrahydro-pyran
• 英文别名: (3R,4S,5R,6R)-2,3,4,5-tetrakis(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxane
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: UCHNNEUPIPRPNU-AWGDKMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  mesna 、 (3R,4S,5R,6R)-2,3,4,5-Tetrakis-allyloxy-6-allyloxymethyl-tetrahydro-pyran 在 偶氮二异丁腈 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 penta-O-(3-{[(sodium oxysulfonyl)ethyl]thio}propyl)-β-D-glucopyranose
  参考文献：
  名称：

  Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. 6. Micelle-like Anti-HIV Polyanionic Compounds Based on a Carbohydrate Core

  摘要：

  A new class of polyanionic compounds, inhibitors of human immunodeficiency virus, was obtained from radical addition of mercapto acid or mercapto ester on a perallylated carbohydrate under UV irradiation with a catalytic amount of AIBN. Unlike the polyanions that we have previously prepared by polymerization reactions, the compounds are structurally well defined. Polyanions bearing 16 carboxylate groups showed a 50% inhibitory concentration (IC50) of 0.1-4.1 mu g/mL against HIV-1 in MT-4 cells while not being toxic to the host cells at concentrations up to 125 mu g/mL. The most potent polyanions also proved active against human cytomegalovirus at concentrations of 1-14 mu g/mL. No activity was observed against any of the other viruses tested (i.e., herpes simplex virus, vesicular stomatitis virus, Sindbis, Semliki forest, parainfluenza-3, Junin, Tacaribe, Coxsackie B4, polio-1, reo-1, or vaccinia virus).

  DOI：

  10.1021/jm960348y
• 作为产物：
  描述：

  D-葡萄糖 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到(3R,4S,5R,6R)-2,3,4,5-Tetrakis-allyloxy-6-allyloxymethyl-tetrahydro-pyran
  参考文献：
  名称：

  Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. 6. Micelle-like Anti-HIV Polyanionic Compounds Based on a Carbohydrate Core

  摘要：

  A new class of polyanionic compounds, inhibitors of human immunodeficiency virus, was obtained from radical addition of mercapto acid or mercapto ester on a perallylated carbohydrate under UV irradiation with a catalytic amount of AIBN. Unlike the polyanions that we have previously prepared by polymerization reactions, the compounds are structurally well defined. Polyanions bearing 16 carboxylate groups showed a 50% inhibitory concentration (IC50) of 0.1-4.1 mu g/mL against HIV-1 in MT-4 cells while not being toxic to the host cells at concentrations up to 125 mu g/mL. The most potent polyanions also proved active against human cytomegalovirus at concentrations of 1-14 mu g/mL. No activity was observed against any of the other viruses tested (i.e., herpes simplex virus, vesicular stomatitis virus, Sindbis, Semliki forest, parainfluenza-3, Junin, Tacaribe, Coxsackie B4, polio-1, reo-1, or vaccinia virus).

  DOI：

  10.1021/jm960348y